Substituted N-(1,2,4-Triazol-3-yl)Arylcarboxamide Compounds and Their Use as Herbicides

ABSTRACT

The invention relates to N-(1,2,4-triazol-3-yl)arylcarboxamides of formula I and their use as herbicides. In said formula I, X represents N or CR 2 , whereas R 1 , R 2 , R 3 , R 4 , R 5 , R 6  and R 7  represent groups such as hydrogen, halogen or organic groups such as alkyl or phenyl.

The present invention relates to substituted N-(1,2,4-triazol-3-yl)arylcarboxamide compounds and the N-oxides and salts thereof and to compositions comprising the same. The invention also relates to the use of the N-(1,2,4-triazol-3-yl)arylcarboxamide compounds or of the compositions comprising such compounds for controlling unwanted vegetation. Furthermore, the invention relates to methods of applying such compounds.

For the purposes of controlling unwanted vegetation, especially in crops, there is an ongoing need for new herbicides which have high activities and selectivities together with a substantial lack of toxicity for humans and animals.

WO 2012/028579 describes N-(tetrazol-4-yl)- and N-(triazol-3-yl)arylcarboxylic acid amides carrying 3 substituents in the 2-, 3- and 4-positions of the aryl ring and their use as herbicides.

WO2013/087577 describes certain N-(tetrazol-4-yl) and N-(triazol-3-yl)arylcarboxylic acid amides, which additionally carry a substituent on the benzamide nitrogen and their use as herbicides.

WO2013/144234 also discloses 1,2,4-triazole derivatives as herbicides.

The compounds of the prior art often suffer form insufficient herbicidal activity in particular at low application rates and/or unsatisfactory selectivity resulting in a low compatibility with crop plants.

Accordingly, it is an object of the present invention to provide further N-(1,2,4-triazol-3-yl)arylcarboxamide compounds having a strong herbicidal activity, in particular even at low application rates, a sufficiently low toxicity for humans and animals and/or a high compatibility with crop plants. The N-(1,2,4-triazol-3-yl)arylcarboxamide compounds should also show a broad activity spectrum against a large number of different unwanted plants.

These and further objectives are achieved by the compounds of formula I defined below and their N-oxides and also their agriculturally suitable salts.

It has been found that the above objectives can be achieved by substituted N-(1,2,4-triazol-3-yl)arylcarboxamide compounds of the general formula I, as defined below, including their N-oxides and their salts, in particular their agriculturally suitable salts.

Therefore, in a first aspect the present invention relates to compounds of formula I,

wherein

-   -   R¹ is selected from the group consisting of cyano-Z¹, halogen,         nitro, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,         C₃-C₁₀-cycloalkyl-Z¹, C₁-C₈-haloalkyl, C₂-C₈-haloalkenyl,         C₃-C₈-haloalkynyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹,         R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹, and heterocyclyloxy-Z¹, where         heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic         or 8-, 9- or 10-membered bicyclic saturated, partially         unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4         heteroatoms as ring members, which are selected from the group         consisting of O, N and S, where the cyclic groups in phenoxy and         heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4         groups R¹¹, which are identical or different;     -   X is N or CR²;     -   R², R³ are identical or different and independently selected         from the group consisting of hydrogen, halogen, OH—Z², NO₂—Z²,         cyano-Z², C₁-C₆-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl,         C₃-C₁₀-cycloalkyl-Z², C₃-C₁₀-cycloalkoxy-Z², where the         C₃-C₁₀-cycloalkyl groups in the two aforementioned radicals are         unsubstituted or partially or completely halogenated,         C₁-C₈-haloalkyl, C₂-C₈-haloalkenyl, C₃-C₈-haloalkynyl,         C₁-C₈-alkoxy-Z², C₁-C₈-haloalkoxy-Z²,         C₃-C₁₀-cycloalkyl-C₁-C₂-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z²,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z², C₂-C₈-alkenyloxy-Z²,         C₂-C₈-alkynyloxy-Z², C₂-C₈-haloalkenyloxy-Z²,         C₃-C₈-haloalkynyloxy-Z², C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z²,         (tri-C₁-C₄-alkyl)silyl-Z², R^(2b)—S(O)_(k)—Z², R^(2c)—C(═O)—Z²,         R^(2d)O—C(═O)—Z², R^(2d)O—N═CH—Z²,         R^(2c)R^(2d)C═N—O—C₁-C₄-alkyl, R^(2e)R^(2f) N—C(═O)—Z²,         R^(2g)R^(2h)N—Z², phenyl-Z^(2a) and heterocyclyl-Z^(2a), where         heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9-         or 10-membered bicyclic saturated, partially unsaturated or         aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as         ring members, which are selected from the group consisting of O,         N and S, where the cyclic groups in phenyl-Z^(2a) and         heterocyclyl-Z^(2a) are unsubstituted or substituted by 1, 2, 3         or 4 groups R²¹, which are identical or different; or     -   R² and R³ together form a saturated 5- or 6-membered ring,         optionally containing an oxygen or a S(O)_(n) heteroatom, the 5-         or 6-membered ring being unsubstituted or substituted by 1, 2 or         3 groups, which are identical or different and selected from the         group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and         C₁-C₄-alkoxy;     -   R⁴ is selected from the group consisting of hydrogen, cyano-Z¹,         halogen, nitro, C₁-C₈-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₂-C₈-alkenyl,         C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino,         C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k),         C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹,         R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, where         heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic         or 8-, 9- or 10-membered bicyclic saturated, partially         unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4         heteroatoms as ring members, which are selected from the group         consisting of O, N and S, where the cyclic groups in phenoxy and         heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4         groups R¹¹, which are identical or different;     -   R⁵ is selected from the group consisting of cyano-Z¹, halogen,         nitro, C₁-C₈-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₂-C₈-alkenyl,         C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino,         C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k),         C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy,         C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹,         R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z, where         heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic         or 8-, 9- or 10-membered bicyclic saturated, partially         unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4         heteroatoms as ring members, which are selected from the group         consisting of O, N and S, where the cyclic groups in phenoxy and         heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4         groups R¹¹, which are identical or different;     -   R⁶ is selected from the group consisting of hydrogen, CN, nitro,         hydroxy, amino, C₁-C₆-alkyl, C₁-C₆-cyano-alkyl,         C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the         C₃-C₇-cycloalkyl groups in the two aforementioned radicals are         unsubstituted or partially or completely halogenated,         C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl,         C₁-C₆-alkyaminocarbonyl, C₁-C₆-dialkyl-aminocarbonyl,         C₁-C₆-alkyamino, C₁-C₆-dialkyl-amino, C₂-C₆-alkenyl,         C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂₋₆-haloalkynyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,         R^(b)R^(b)N—S(O)_(n)—Z, R^(b)O—S(O)_(n)—Z, R^(b)—S(O)_(n)—Z,         R^(c)R^(c)N—C₁-C₃-alkyl-S(O)_(n)—C₁-C₃-alkyl,         R^(c)—C(═O)—C₁-C₃-alkyl, R^(d)—C(═O)O—C₁-C₃-alkyl,         R^(d)—O—C(═O)O—C₁-C₃-alkyl, R^(d)O—C(═O)—C₁-C₃-alkyl,         R^(e)R^(f)N—C(═O)—C₁-C₃-alkyl, R^(c)—C(═O)R^(e)N—C₁-C₃-alkyl,         R^(b)—S(O)_(n)—R^(e)N—C₁-C₃-alkyl, R^(c)R^(c)N—C₁-C₃-alkyl,         phenyl-Z and heterocyclyl-Z, where heterocyclyl is a 5- or         6-membered monocyclic or 8-, 9- or 10-membered bicyclic         saturated, partially unsaturated or aromatic heterocycle, which         contains 1, 2, 3 or 4 heteroatoms as ring members, which are         selected from the group consisting of O, N and S, where phenyl         and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or         4 groups R′, which are identical or different;     -   R⁷ is selected from the group consisting of C₁-C₆-alkyl,         C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the         C₃-C₇-cycloalkyl groups in the two aforementioned radicals are         unsubstituted or partially or completely halogenated,         C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy,         C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-haloalkoxy-C₁-C₄-alkyl;     -   n is 0, 1 or 2;     -   k is 0, 1 or 2;     -   R′, R¹¹, R²¹ independently of each other are selected from the         group consisting of halogen, NO₂, CN, C₁-C₆-alkyl,         C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₁-C₆-haloalkyl,         C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,         C₂-C₆-haloalkynyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl,         C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₃-C₇-cycloalkoxy and         C₁-C₆-haloalkyloxy, or two vicinal radicals R′, R¹¹ or R²¹         together may form a group ═O;     -   Z, Z¹, Z² independently of each other are selected from the         group consisting of a covalent bond and C₁-C₄-alkanediyl;     -   Z^(2a) is selected from the group consisting of a covalent bond,         C₁-C₄-alkanediyl, O—C₁-C₄-alkanediyl, C₁-C₄-alkanediyl-O and         C₁-C₄-alkanediyl-O—C₁-C₄-alkanediyl;     -   R^(b), R^(1b), R^(2b) independently of each other are selected         from the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl and heterocyclyl, where         heterocyclyl is a 5- or 6-membered monocyclic saturated,         partially unsaturated or aromatic heterocycle, which contains 1,         2, 3 or 4 heteroatoms as ring members, which are selected from         the group consisting of O, N and S, where phenyl and         heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4         groups, which are identical or different and selected from the         group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;     -   R^(c), R^(2c) independently of each other are selected from the         group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₁-C₆-haloalkyl,         C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,         C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl and         heterocyclyl, where heterocyclyl is a 5- or 6-membered         monocyclic saturated, partially unsaturated or aromatic         heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring         members, which are selected from the group consisting of O, N         and S, where phenyl, benzyl and heterocyclyl are unsubstituted         or substituted by 1, 2, 3 or 4 groups, which are identical or         different and selected from the group consisting of halogen,         C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;     -   R^(d), R^(2d) independently of each other are selected from the         group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₁-C₆-haloalkyl,         C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,         C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl,         where phenyl and benzyl are unsubstituted or substituted by 1,         2, 3 or 4 groups, which are identical or different and selected         from the group consisting of halogen, C₁-C₄-alkyl,         C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;     -   R^(e), R^(f) independently of each other are selected from the         group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl,         C₃-C₇-cycloalkyl-C₁-C₄-alkyl, where the C₃-C₇-cycloalkyl groups         in the two aforementioned radicals are unsubstituted or         partially or completely halogenated, C₁-C₆-haloalkyl,         C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl,         C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl,         where phenyl and benzyl are unsubstituted or substituted by 1,         2, 3 or 4 groups, which are identical or different and selected         from the group consisting of halogen, C₁-C₄-alkyl,         C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or     -   R^(e), R^(f) together with the nitrogen atom, to which they are         bound may form a 5-, 6 or 7-membered, saturated or unsaturated         N-bound heterocyclic radical, which may carry as a ring member a         further heteroatom selected from O, S and N and which is         unsubstituted or may carry 1, 2, 3 or 4 groups, which are         identical or different and selected from the group consisting of         halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and         C₁-C₄-haloalkoxy;     -   R^(2e), R^(2f) independently of each other have the meanings         given for R^(e), R^(f);     -   R^(g) is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,         where the C₃-C₇-cycloalkyl groups in the two aforementioned         radicals are unsubstituted or partially or completely         halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl and benzyl,         where phenyl and benzyl are unsubstituted or substituted by 1,         2, 3 or 4 groups, which are identical or different and selected         from the group consisting of halogen, C₁-C₄-alkyl,         C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy;     -   R^(h) is selected from the group consisting of hydrogen,         C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl,         where the C₃-C₇-cycloalkyl groups in the two aforementioned         radicals are unsubstituted or partially or completely         halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl,         C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, a radical C(═O)—R^(k),         phenyl and benzyl, where phenyl and benzyl are unsubstituted or         substituted by 1, 2, 3 or 4 groups, which are identical or         different and selected from the group consisting of halogen,         C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy,         or     -   R^(g), R^(h) together with the nitrogen atom, to which they are         bound may form a 5-, 6 or 7-membered, saturated or unsaturated         N-bound heterocyclic radical, which may carry as a ring member a         further heteroatom selected from O, S and N and which is         unsubstituted or may carry 1, 2, 3 or 4 groups, which are         identical or different and selected from the group consisting of         ═O, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and         C₁-C₄-haloalkoxy;     -   R^(2g), R^(2h) independently of each other have the meanings         given for R^(g), R^(h);     -   R^(k) has the meanings given for R^(c);     -   an N-oxide or an agriculturally suitable salt thereof.

The compounds of the present invention, i.e. the compounds of formula I, their N-oxides, or their salts are particularly useful for controlling unwanted vegetation. Therefore, the invention also relates to the use of a compound of the present invention, an N-oxide or a salt thereof or of a composition comprising at least one compound of the invention, an N-oxide or an agriculturally suitable salt thereof for combating or controlling unwanted vegetation.

The invention also relates to a composition comprising at least one compound according to the invention, including an N-oxide or a salt thereof, and at least one auxiliary. In particular, the invention relates to an agricultural composition comprising at least one compound according to the invention including an N-oxide or an agriculturally suitable salt thereof, and at least one auxiliary customary for crop protection formulations.

The present invention also relates to a method for combating or controlling unwanted vegetation, which method comprises allowing a herbicidally effective amount of at least one compound according to the invention, including an N-oxide or a salt thereof, to act on unwanted plants, their seed and/or their habitat.

Depending on the substitution pattern, the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.

The invention provides both the pure enantiomers or pure diastereomers of the compounds of formula I, and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula I or its mixtures. Suitable compounds of formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be present with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group. The term “stereoisomer(s)” encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).

Depending on the substitution pattern, the compounds of formula I may be present in the form of their tautomers. Hence the invention also relates to the tautomers of the formula I and the stereoisomers, salts and N-oxides of said tautomers.

The term “N-oxide” includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety. N-oxides in compounds of formula I can in particular be prepared by oxidizing the ring nitrogen atom(s) of the N-(1,2,4-triazol-3-yl)arylcarboxamide ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides, or the ring nitrogen atom(s) of a heterocyclic substituent R, R¹, R² or R³.

The present invention moreover relates to compounds as defined herein, wherein one or more of the atoms depicted in formula I have been replaced by its stable, preferably non-radioactive isotope (e.g., hydrogen by deuterium, ¹²C by ¹³C, ¹⁴N by ¹⁵N, ¹⁶O by ¹⁸O) and in particular wherein at least one hydrogen atom has been replaced by a deuterium atom. Of course, the compounds according to the invention contain more of the respective isotope than this naturally occurs and thus is anyway present in the compounds of formula I.

The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of formula I, their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula I, its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.

Salts of the compounds of the present invention are preferably agriculturally suitable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.

Useful agriculturally suitable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the herbicidal action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH₄ ⁺) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethylammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compounds of the present invention with an acid of the corresponding anion, preferably with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

The term “undesired vegetation” (“weeds”) is understood to include any vegetation growing in non-crop-areas or at a crop plant site or locus of seeded and otherwise desired crop, where the vegetation is any plant species, including their germinant seeds, emerging seedlings and established vegetation, other than the seeded or desired crop (if any). Weeds, in the broadest sense, are plants considered undesirable in a particular location.

The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual group members. The prefix C_(n)-C_(m) indicates in each case the possible number of carbon atoms in the group.

The term “halogen” denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

The term “partially or completely halogenated” will be taken to mean that 1 or more, e.g. 1, 2, 3, 4 or 5 or all of the hydrogen atoms of a given radical have been replaced by a halogen atom, in particular by fluorine or chlorine. A partially or completely halogenated radical is termed below also “halo-radical”. For example, partially or completely halogenated alkyl is also termed haloalkyl.

The term “alkyl” as used herein (and in the alkyl moieties of other groups comprising an alkyl group, e.g. alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylthio, alkylsulfonyl and alkoxyalkyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 10 carbon atoms, frequently from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms. Examples of C₁-C₄-alkyl are methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl (sec-butyl), isobutyl and tert-butyl. Examples for C₁-C₆-alkyl are, apart those mentioned for C₁-C₄-alkyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Examples for C₁-C₁₀-alkyl are, apart those mentioned for C₁-C₆-alkyl, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, n-octyl, 1-methyloctyl, 2-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 1,2-dimethylhexyl, 1-propylpentyl, 2-propylpentyl, nonyl, decyl, 2-propylheptyl and 3-propylheptyl.

The term “alkylene” (or alkanediyl) as used herein in each case denotes an alkyl radical as defined above, wherein one hydrogen atom at any position of the carbon backbone is replaced by one further binding site, thus forming a bivalent moiety.

The term “haloalkyl” as used herein (and in the haloalkyl moieties of other groups comprising a haloalkyl group, e.g. haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkylsulfonyl and haloalkylsulfinyl) denotes in each case a straight-chain or branched alkyl group having usually from 1 to 8 carbon atoms (“C₁-C₈-haloalkyl”), frequently from 1 to 6 carbon atoms (“C₁-C₆-haloalkyl”), more frequently 1 to 4 carbon atoms (“C₁-C₄-haloalkyl”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from C₁-C₄-haloalkyl, more preferably from C₁-C₂-haloalkyl, more preferably from halomethyl, in particular from C₁-C₂-fluoroalkyl. Halomethyl is methyl in which 1, 2 or 3 of the hydrogen atoms are replaced by halogen atoms. Examples are bromomethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl and the like. Examples for C₁-C₂-fluoroalkyl are fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like. Examples for C₁-C₂-haloalkyl are, apart those mentioned for C₁-C₂-fluoroalkyl, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 2-chloroethyl, 2,2,-dichloroethyl, 2,2,2-trichloroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 1-bromoethyl, and the like. Examples for C₁-C₄-haloalkyl are, apart those mentioned for C₁-C₂-haloalkyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 3,3-difluoropropyl, 3,3,3-trifluoropropyl, heptafluoropropyl, 1,1,1-trifluoroprop-2-yl, 3-chloropropyl, 4-chlorobutyl and the like.

The term “cycloalkyl” as used herein (and in the cycloalkyl moieties of other groups comprising a cycloalkyl group, e.g. cycloalkoxy and cycloalkylalkyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms (“C₃-C₁₀-cycloalkyl”), preferably 3 to 7 carbon atoms (“C₃-C₇-cycloalkyl”) or in particular 3 to 6 carbon atoms (“C₃-C₆-cycloalkyl”). Examples of monocyclic radicals having 3 to 6 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of monocyclic radicals having 3 to 7 carbon atoms comprise cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl. Examples of bicyclic radicals having 7 or 8 carbon atoms comprise bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl, bicyclo[3.1.1]heptyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl and bicyclo[3.2.1]octyl.

The term “halocycloalkyl” as used herein (and in the halocycloalkyl moieties of other groups comprising an halocycloalkyl group, e.g. halocycloalkylmethyl) denotes in each case a mono- or bicyclic cycloaliphatic radical having usually from 3 to 10 carbon atoms, preferably 3 to 7 carbon atoms or in particular 3 to 6 carbon atoms, wherein at least one, e.g. 1, 2, 3, 4 or 5 of the hydrogen atoms are replaced by halogen, in particular by fluorine or chlorine. Examples are 1- and 2-fluorocyclopropyl, 1,2-, 2,2- and 2,3-difluorocyclopropyl, 1,2,2-trifluorocyclopropyl, 2,2,3,3-tetrafluorocyclpropyl, 1- and 2-chlorocyclopropyl, 1,2-, 2,2- and 2,3-dichlorocyclopropyl, 1,2,2-trichlorocyclopropyl, 2,2,3,3-tetrachlorocyclpropyl, 1-,2- and 3-fluorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-difluorocyclopentyl, 1-,2- and 3-chlorocyclopentyl, 1,2-, 2,2-, 2,3-, 3,3-, 3,4-, 2,5-dichlorocyclopentyl and the like.

The term “cycloalkyl-alkyl” used herein denotes a cycloalkyl group, as defined above, which is bound to the remainder of the molecule via an alkylene group. The term “C₃-C₇-cycloalkyl-C₁-C₄-alkyl” refers to a C₃-C₇-cycloalkyl group as defined above which is bound to the remainder of the molecule via a C₁-C₄-alkyl group, as defined above. Examples are cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclobutylmethyl, cyclobutylethyl, cyclobutylpropyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylethyl, cyclohexylpropyl, and the like.

The term “alkenyl” as used herein denotes in each case a monounsaturated straight-chain or branched hydrocarbon radical having usually 2 to 8 (“C₂-C₈-alkenyl”), preferably 2 to 6 carbon atoms (“C₂-C₆-alkenyl”), in particular 2 to 4 carbon atoms (“C₂-C₄-alkenyl”), and a double bond in any position, for example C₂-C₄-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl or 2-methyl-2-propenyl; C₂-C₆-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2-propenyl and the like, or C₂-C₈-alkenyl, such as the radicals mentioned for C₂-C₆-alkenyl and additionally 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl and the positional isomers thereof.

The term “haloalkenyl” as used herein, which may also be expressed as “alkenyl which is substituted by halogen”, and the haloalkenyl moieties in haloalkenyloxy and the like refers to unsaturated straight-chain or branched hydrocarbon radicals having 2 to 8 (“C₂-C₈-haloalkenyl”) or 2 to 6 (“C₂-C₆-haloalkenyl”) or 2 to 4 (“C₂-C₄-haloalkenyl”) carbon atoms and a double bond in any position, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine, for example chlorovinyl, chloroallyl and the like.

The term “alkynyl” as used herein denotes unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 (“C₂-C₈-alkynyl”), frequently 2 to 6 (“C₂-C₆-alkynyl”), preferably 2 to 4 carbon atoms (“C₂-C₄-alkynyl”) and a triple bond in any position, for example C₂-C₄-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl and the like, C₂-C₆-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl and the like.

The term “haloalkynyl” as used herein, which is also expressed as “alkynyl which is substituted by halogen”, refers to unsaturated straight-chain or branched hydrocarbon radicals having usually 2 to 8 carbon atoms (“C₂-C₈-haloalkynyl”), frequently 2 to 6 (“C₂-C₆-haloalkynyl”), preferably 2 to 4 carbon atoms (“C₂-C₄-haloalkynyl”), and a triple bond in any position (as mentioned above), where some or all of the hydrogen atoms in these groups are replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine.

The term “alkoxy” as used herein denotes in each case a straight-chain or branched alkyl group usually having from 1 to 8 carbon atoms (“C₁-C₈-alkoxy”), frequently from 1 to 6 carbon atoms (“C₁-C₆-alkoxy”), preferably 1 to 4 carbon atoms (“C₁-C₄-alkoxy”), which is bound to the remainder of the molecule via an oxygen atom. C₁-C₂-Alkoxy is methoxy or ethoxy. C₁-C₄-Alkoxy is additionally, for example, n-propoxy, 1-methylethoxy (isopropoxy), butoxy, 1-methylpropoxy (sec-butoxy), 2-methylpropoxy (isobutoxy) or 1,1-dimethylethoxy (tert-butoxy). C₁-C₆-Alkoxy is additionally, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy. C₁-C₈-Alkoxy is additionally, for example, heptyloxy, octyloxy, 2-ethylhexyloxy and positional isomers thereof.

The term “haloalkoxy” as used herein denotes in each case a straight-chain or branched alkoxy group, as defined above, having from 1 to 8 carbon atoms (“C₁-C₈-haloalkoxy”), frequently from 1 to 6 carbon atoms (“C₁-C₆-haloalkoxy”), preferably 1 to 4 carbon atoms (“C₁-C₄-haloalkoxy”), more preferably 1 to 3 carbon atoms (“C₁-C₃-haloalkoxy”), wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms, in particular fluorine atoms. C₁-C₂-Haloalkoxy is, for example, OCH₂F, OCHF₂, OCF₃, OCH₂Cl, OCHCl₂, OCCl₃, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy or OC₂F₅. C₁-C₄-Haloalkoxy is additionally, for example, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH₂—C₂F₅, OCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethoxy, 1-(CH₂Cl)-2-chloroethoxy, 1-(CH₂Br)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy. C₁-C₆-Haloalkoxy is additionally, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-brompentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy.

The term “alkoxyalkyl” as used herein denotes in each case alkyl usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. “C₁-C₆-alkoxy-C₁-C₆-alkyl” is a C₁-C₆-alkyl group, as defined above, in which one hydrogen atom is replaced by a C₁-C₆-alkoxy group, as defined above. Examples are CH₂OCH₃, CH₂—OC₂H₅, n-propoxymethyl, CH₂—OCH(CH₃)₂, n-butoxymethyl, (1-methylpropoxy)-methyl, (2-methylpropoxy)methyl, CH₂—OC(CH₃)₃, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)-ethyl, 2-(1-methylethoxy)-ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)-ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1,1-dimethylethoxy)-ethyl, 2-(methoxy)-propyl, 2-(ethoxy)-propyl, 2-(n-propoxy)-propyl, 2-(1-methylethoxy)-propyl, 2-(n-butoxy)-propyl, 2-(1-methylpropoxy)-propyl, 2-(2-methylpropoxy)-propyl, 2-(1,1-dimethylethoxy)-propyl, 3-(methoxy)-propyl, 3-(ethoxy)-propyl, 3-(n-propoxy)-propyl, 3-(1-methylethoxy)-propyl, 3-(n-butoxy)-propyl, 3-(1-methylpropoxy)-propyl, 3-(2-methylpropoxy)-propyl, 3-(1,1-dimethylethoxy)-propyl, 2-(methoxy)-butyl, 2-(ethoxy)-butyl, 2-(n-propoxy)-butyl, 2-(1-methylethoxy)-butyl, 2-(n-butoxy)-butyl, 2-(1-methylpropoxy)-butyl, 2-(2-methyl-propoxy)-butyl, 2-(1,1-dimethylethoxy)-butyl, 3-(methoxy)-butyl, 3-(ethoxy)-butyl, 3-(n-propoxy)-butyl, 3-(1-methylethoxy)-butyl, 3-(n-butoxy)-butyl, 3-(1-methylpropoxy)-butyl, 3-(2-methylpropoxy)-butyl, 3-(1,1-dimethylethoxy)-butyl, 4-(methoxy)-butyl, 4-(ethoxy)-butyl, 4-(n-propoxy)-butyl, 4-(1-methylethoxy)-butyl, 4-(n-butoxy)-butyl, 4-(1-methylpropoxy)-butyl, 4-(2-methylpropoxy)-butyl, 4-(1,1-dimethylethoxy)-butyl and the like.

The term “haloalkoxy-alkyl” as used herein denotes in each case alkyl as defined above, usually comprising 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein 1 carbon atom carries an haloalkoxy radical as defined above, usually comprising 1 to 8, frequently 1 to 6, in particular 1 to 4, carbon atoms as defined above. Examples are fluoromethoxymethyl, difluoromethoxymethyl, trifluoromethoxymethyl, 1-fluoroethoxymethyl, 2-fluoroethoxymethyl, 1,1-difluoroethoxymethyl, 1,2-difluoroethoxymethyl, 2,2-difluoroethoxymethyl, 1,1,2-trifluoroethoxymethyl, 1,2,2-trifluoroethoxymethyl, 2,2,2-trifluoroethoxymethyl, pentafluoroethoxymethyl, 1-fluoroethoxy-1-ethyl, 2-fluoroethoxy-1-ethyl, 1,1-difluoroethoxy-1-ethyl, 1,2-difluoroethoxy-1-ethyl, 2,2-difluoroethoxy-1-ethyl, 1,1,2-trifluoroethoxy-1-ethyl, 1,2,2-trifluoroethoxy-1-ethyl, 2,2,2-trifluoroethoxy-1-ethyl, pentafluoroethoxy-1-ethyl, 1-fluoroethoxy-2-ethyl, 2-fluoroethoxy-2-ethyl, 1,1-difluoroethoxy-2-ethyl, 1,2-difluoroethoxy-2-ethyl, 2,2-difluoroethoxy-2-ethyl, 1,1,2-trifluoroethoxy-2-ethyl, 1,2,2-trifluoroethoxy-2-ethyl, 2,2,2-trifluoroethoxy-2-ethyl, pentafluoroethoxy-2-ethyl, and the like.

The term “alkylthio” (also alkylsulfanyl, “alkyl-S” or “alkyl-S(O)_(k)” (wherein k is 0)) as used herein denotes in each case a straight-chain or branched saturated alkyl group as defined above, usually comprising 1 to 8 carbon atoms (“C₁-C₈-alkylthio”), frequently comprising 1 to 6 carbon atoms (“C₁-C₆-alkylthio”), preferably 1 to 4 carbon atoms (“C₁-C₄-alkylthio”), which is attached via a sulfur atom at any position in the alkyl group. C₁-C₂-Alkylthio is methylthio or ethylthio. C₁-C₄-Alkylthio is additionally, for example, n-propylthio, 1-methylethylthio (isopropylthio), butylthio, 1-methylpropylthio (sec-butylthio), 2-methylpropylthio (isobutylthio) or 1,1-dimethylethylthio (tert-butylthio). C₁-C₆-Alkylthio is additionally, for example, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio. C₁-C₈-Alkylthio is additionally, for example, heptylthio, octylthio, 2-ethylhexylthio and positional isomers thereof.

The term “haloalkylthio” as used herein refers to an alkylthio group as defined above wherein the hydrogen atoms are partially or completely substituted by fluorine, chlorine, bromine and/or iodine. C₁-C₂-Haloalkylthio is, for example, SCH₂F, SCHF₂, SCF₃, SCH₂Cl, SCHCl₂, SCCl₃, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio or SC₂F₅. C₁-C₄-Haloalkylthio is additionally, for example, 2-fluoropropylthio, 3-fluoropropylthio, 2,2-difluoropropyithio, 2,3-difluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2,3-dichloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, SCH₂—C₂F₅, SCF₂—C₂F₅, 1-(CH₂F)-2-fluoroethylthio, 1-(CH₂Cl)-2-chloroethylthio, 1-(CH₂Br)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio. C₁-C₆-Haloalkylthio is additionally, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-brompentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio.

The terms “alkylsulfinyl” and “alkyl-S(O)_(k)” (wherein k is 1) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfinyl [S(O)] group. For example, the term “C₁-C₂-alkylsulfinyl” refers to a C₁-C₂-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C₁-C₄-alkylsulfinyl” refers to a C₁-C₄-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. The term “C₁-C₆-alkylsulfinyl” refers to a C₁-C₆-alkyl group, as defined above, attached via a sulfinyl [S(O)] group. C₁-C₂-alkylsulfinyl is methylsulfinyl or ethylsulfinyl. C₁-C₄-alkylsulfinyl is additionally, for example, n-propylsulfinyl, 1-methylethylsulfinyl (isopropylsulfinyl), butylsulfinyl, 1-methylpropylsulfinyl (sec-butylsulfinyl), 2-methylpropylsulfinyl (isobutylsulfinyl) or 1,1-dimethylethylsulfinyl (tert-butylsulfinyl). C₁-C₆-alkylsulfinyl is additionally, for example, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl.

The terms “alkylsulfonyl” and “alkyl-S(O)_(k)” (wherein k is 2) are equivalent and, as used herein, denote an alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. The term “C₁-C₂-alkylsulfonyl” refers to a C₁-C₂-alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. The term “C₁-C₄-alkylsulfonyl” refers to a C₁-C₄-alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. The term “C₁-C₆-alkylsulfonyl” refers to a C₁-C₆-alkyl group, as defined above, attached via a sulfonyl [S(O)₂] group. C₁-C₂-alkylsulfonyl is methylsulfonyl or ethylsulfonyl. C₁-C₄-alkylsulfonyl is additionally, for example, n-propylsulfonyl, 1-methylethylsulfonyl (isopropylsulfonyl), butylsulfonyl, 1-methylpropylsulfonyl (sec-butylsulfonyl), 2-methylpropylsulfonyl (isobutylsulfonyl) or 1,1-dimethylethylsulfonyl (tert-butylsulfonyl). C₁-C₆-alkylsulfonyl is additionally, for example, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl.

The term “alkylamino” as used herein denotes in each case a group R*HN—, wherein R* is a straight-chain or branched alkyl group usually having from 1 to 6 carbon atoms (“C₁-C₆-alkylamino”), preferably 1 to 4 carbon atoms (“C₁-C₄-alkylamino”). Examples of C₁-C₆-alkylamino are methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, 2-butylamino, isobutylamino, tert-butylamino, and the like.

The term “dialkylamino” as used herein denotes in each case a group R*R°N—, wherein R* and R°, independently of each other, are a straight-chain or branched alkyl group each usually having from 1 to 6 carbon atoms (“di-(C₁-C₆-alkyl)-amino”), preferably 1 to 4 carbon atoms (“di-(C₁-C₄-alkyl)-amino”). Examples of a di-(C₁-C₆-alkyl)-amino group are dimethylamino, diethylamino, dipropylamino, dibutylamino, methyl-ethyl-amino, methyl-propyl-amino, methyl-isopropylamino, methyl-butyl-amino, methyl-isobutyl-amino, ethyl-propyl-amino, ethyl-isopropylamino, ethyl-butyl-amino, ethyl-isobutyl-amino, and the like.

The suffix “-carbonyl” in a group denotes in each case that the group is bound to the remainder of the molecule via a carbonyl C═O group. This is the case e.g. in alkylcarbonyl, haloalkylcarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonyl, haloalkoxycarbonyl.

The term “aryl” as used herein refers to a mono-, bi- or tricyclic aromatic hydrocarbon radical such as phenyl or naphthyl, in particular phenyl.

The term “het(ero)aryl” as used herein refers to a mono-, bi- or tricyclic heteroaromatic hydrocarbon radical, preferably to a monocyclic heteroaromatic radical, such as pyridyl, pyrimidyl and the like.

The term “3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms as ring members selected from the groups consisting of N, O and S” as used herein denotes monocyclic or bicyclic radicals, the monocyclic or bicyclic radicals being saturated, unsaturated or aromatic where N can optionally be oxidized, i.e. in the form of an N-oxide, and S can also optionally be oxidized to various oxidation states, i.e. as SO or SO₂. An unsaturated heterocycle contains at least one C—C and/or C—N and/or N—N double bond(s). A fully unsaturated heterocycle contains as many conjugated C—C and/or C—N and/or N—N double bonds as allowed by the size(s) of the ring(s). An aromatic monocyclic heterocycle is a fully unsaturated 5- or 6-membered monocyclic heterocycle. An aromatic bicyclic heterocycle is an 8-, 9- or 10-membered bicyclic heterocycle consisting of a 5- or 6-membered heteroaromatic ring which is fused to a phenyl ring or to another 5- or 6-membered heteroaromatic ring. The heterocycle may be attached to the remainder of the molecule via a carbon ring member or via a nitrogen ring member. As a matter of course, the heterocyclic ring contains at least one carbon ring atom. If the ring contains more than one O ring atom, these are not adjacent.

Examples of a 3-, 4-, 5- or 6-membered monocyclic saturated heterocycle include: oxirane-2-yl, aziridine-1-yl, aziridine-2-yl, oxetan-2-yl, azetidine-1-yl, azetidine-2-yl, azetidine-3-yl, thietane-1-yl, thietan-2-yl, thietane-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, pyrazolidin-1-yl, pyrazolidin-3-yl, pyrazolidin-4-yl, pyrazolidin-5-yl, imidazolidin-1-yl, imidazolidin-2-yl, imidazolidin-4-yl, oxazolidin-2-yl, oxazolidin-3-yl, oxazolidin-4-yl, oxazolidin-5-yl, isoxazolidin-2-yl, isoxazolidin-3-yl, isoxazolidin-4-yl, isoxazolidin-5-yl, thiazolidin-2-yl, thiazolidin-3-yl, thiazolidin-4-yl, thiazolidin-5-yl, isothiazolidin-2-yl, isothiazolidin-3-yl, isothiazolidin-4-yl, isothiazolidin-5-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-yl, piperazin-2-yl, 1,3,5-hexahydrotriazin-1-yl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, thiomorpholin-2-yl, thiomorpholin-3-yl, thiomorpholin-4-yl, 1-oxothiomorpholin-2-yl, 1-oxothiomorpholin-3-yl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-2-yl, 1,1-dioxothiomorpholin-3-yl, 1,1-dioxothiomorpholin-4-yl and the like.

Examples of a 5- or 6-membered monocyclic partially unsaturated heterocycle include: 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-, 3-, 4-, 5- or 6-di- or tetrahydropyridinyl, 3-di- or tetrahydropyridazinyl, 4-di- or tetrahydropyridazinyl, 2-di- or tetrahydropyrimidinyl, 4-di- or tetrahydropyrimidinyl, 5-di- or tetrahydropyrimidinyl, di- or tetrahydropyrazinyl, 1,3,5-di- or tetrahydrotriazin-2-yl and 1,2,4-di- or tetrahydrotriazin-3-yl.

A 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring is e.g. a 5- or 6-membered monocyclic fully unsaturated (including aromatic) heterocyclic ring. Examples are: 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl, 1,3,4-triazol-1-yl, 1,3,4-triazol-2-yl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-oxopyridin-2-yl, 1-oxopyridin-3-yl, 1-oxopyridin-4-yl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl and 2-pyrazinyl.

Examples of a 5- or 6-membered heteroaromatic ring fused to a phenyl ring or to a 5- or 6-membered heteroaromatic radical include benzofuranyl, benzothienyl, indolyl, indazolyl, benzimidazolyl, benzoxathiazolyl, benzoxadiazolyl, benzothiadiazolyl, benzoxazinyl, chinolinyl, isochinolinyl, purinyl, 1,8-naphthyridyl, pteridyl, pyrido[3,2-d]pyrimidyl or pyridoimidazolyl and the like.

If two radicals bound on the same nitrogen atom (for example R^(e) and R^(f) or R^(2e) and R^(2f) or R^(g) and R^(h) or R^(2g) and R^(2h)) together with the nitrogen atom, to which they are bound, form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N, this is for example pyrrolidine-1-yl, pyrazolidin-1-yl, imidazolidin-1-yl, oxazolidin-3-yl, thiazolidin-3-yl, isoxazolidin-2-yl, isothiazolin-2-yl, [1,2,3]-triazolidin-1-yl, [1,2,3]-triazolidin-2-yl, [1,2,4]-triazolidin-1-yl, [1,2,4]-triazolidin-4-yl, [1,2,3]-oxadiazolidin-2-yl, [1,2,3]-oxadiazolidin-3-yl, [1,2,5]-oxadiazolidin-2-yl, [1,2,4]-oxadiazolidin-2-yl, [1,2,4]-oxadiazolidin-4-yl, [1,3,4]-oxadiazolidin-3-yl, [1,2,3]-thiadiazolidin-2-yl, [1,2,3]-thiadiazolidin-3-yl, [1,2,5]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-2-yl, [1,2,4]-thiadiazolidin-4-yl, [1,3,4]-thiadiazolidin-3-yl, piperdin-1-yl, piperazine-1-yl, morpholin-1-yl, thiomorpholin-1-yl, 1-oxothiomorpholin-1-yl, 1,1-dioxothiomorpholin-1-yl, azepan-1-yl, 1,4-diazepan-1-yl, pyrrolin-1-yl, pyrazolin-1-yl, imidazolin-1-yl, oxazolin-3-yl, isoxazolin-2-yl, thiazolin-3-yl, isothiazolin-1-yl, 1,2-dihydropyridin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1,2-dihydropyridazin, 1,6-dihydropyridazin, 1,2,3,4-tetrahydropyridazin-1-yl, 1,2,5,6-tetrahydropyridazin-1-yl, 1,2-dihydropyrimidin, 1,6-dihydropyrimidin, 1,2,3,4-tetrahydropyrimidin-1-yl, 1,2,5,6-tetrahydropyrimidin-1-yl, 1,2-dihydropyrazin-1-yl, 1,2,3,4-tetrahydropyrazin-1-yl, 1,2,5,6-tetrahydropyrazin-1-yl, pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl, [1,2,3]-1H-triazol-1-yl, [1,2,3]-2H-triazol-2-yl, [1,2,4]-1H-triazol-1-yl and [1,2,4]-4H-triazol-4-yl.

The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers, salts, tautomers or N-oxides thereof.

The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the compounds of formulae I, where applicable, as well as concerning the uses and methods according to the invention and the composition according to the invention.

Preferred compounds according to the invention are compounds of formula I or a stereoisomer, salt or N-oxide thereof, wherein the salt is an agriculturally suitable salt. Further preferred compounds according to the invention are compounds of formula I or an N-oxide or salt thereof, especially an agriculturally suitable salt. Particularly preferred compounds according to the invention are compounds of formula I or a salt thereof, especially an agriculturally suitable salt thereof.

According to one embodiment of the invention the variable X in the compounds of formula I is N.

According to another embodiment of the invention the variable X in the compounds of formula I is CR².

Preferred compounds according to the invention are compounds of formula I, wherein R¹ is selected from the group consisting of CN, halogen, nitro, C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy and R^(1b)—S(O)_(k), where k and Z¹ are as defined herein and where R^(1b) is as defined above and in particular selected from the group consisting of C₁-C₄-alkyl and C₁-C₄-haloalkyl. In this context Z¹ is in particular a covalent bond.

More preferably, R¹ is selected from halogen, CN, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), where k is 0 or 2.

In particular, R¹ is selected from the group consisting of halogen, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and C₁-C₄-alkylsulfonyl, specifically R¹ is F, Cl, Br, NO₂, CH₃, cyclopropyl, CF₃, OCH₃, OCF₃, SCF₃, SO₂CH₃, CH₂OCH₃ or CH₂OCH₂CH₂OCH₃, and more specifically R¹ is Cl, NO₂, CH₃, cyclopropyl, CF₃, SO₂CH₃, CH₂OCH₃ or CH₂OCH₂CH₂OCH₃.

In one group of embodiments of the invention, where X is CR², the variable R² is hydrogen.

In one group of embodiments of the invention, where X is CR², the variable R² of the compounds of formula I has any one of the meanings given above for R² with the exception of hydrogen.

According to preferred embodiment of the invention the variable R² in the compounds of formula I is a 5- or 6-membered heterocyclyl, where heterocyclyl is a saturated, partially unsaturated or aromatic heterocyclic radical, which contains as ring member 1 heteroatom selected from the group consisting of O, N and S and 0, 1, 2 or 3 further nitrogen atom(s), where heterocyclyl is unsubstituted or carries 1, 2 or 3 radicals R²¹, as defined herein, which are identical or different.

According to an even more preferred embodiment of the invention the variable R² in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from the group consisting of isoxazolinyl (4,5-dihydroisoxazolyl), 1,2-dihydrotetrazolonyl, 1,4-dihydrotetrazolonyl, tetrahydrofuryl, dioxolanyl, piperidinyl, morpholinyl, piperazinyl, isoxazolyl, pyrazolyl, thiazolyl, oxazolyl, furyl, pyridinyl, pyrimidinyl and pyrazinyl, where heterocyclyl is unsubstituted or carries 1, 2 or 3 radicals R²¹ which are identical or different and are selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkylthio-C₁-C₄-alkyl.

According to a particular embodiment of the invention the variable R² in the compounds of formula I is a 5- or 6-membered heterocyclyl selected from 4,5-dihydroisoxazol-3-yl, which is unsubstituted or substituted in position 5 with CH₃, CH₂F or CHF₂, 4,5-dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH₃, OCH₃, CH₂OCH₃, CH₂SCH₃, 1-methyl-5-oxo-1,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3-methyl-isoxazol-5-yl, 1-methyl-1H-pyrazol-3-yl, 2-methyl-2H-pyrazol-3-yl and thiazol-2-yl.

According to a preferred embodiment of the invention the variable R² in the compounds of formula I is phenyl-Z^(2a), where Z^(2a) is as defined herein, and where phenyl is unsubstituted or carries 1, 2 or 3 radicals R²¹ which are identical or different and as defined above and which are in particular selected from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkoxy, and preferably from halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkyl and C₁-C₂-alkoxy-C₁-C₂-alkoxy.

According to a more preferred embodiment of the invention the variable R² in the compounds of formula I is a radical of the following formula:

in which # denotes the bond through which the group R² is attached and:

-   R^(P1) is hydrogen or halogen, preferably hydrogen, Cl, Br or F, and     in particular H or F; -   R^(P2) is hydrogen, halogen or C₁-C₂-alkoxy, preferably hydrogen,     Cl, Br, F, OCH₃ or OCH₂CH₃, and in particular H, F, Cl or OCH₃; and -   R^(P3) is hydrogen, halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl,     C₁-C₂-alkoxy, C₁-C₂-alkoxy-C₁-C₂-alkoxy, preferably hydrogen, Cl,     Br, F, CH₃, C₂H₅, CF₃, CHF₂, CH₂F, CCl₂F, CF₂Cl, CH₂CF₃, CH₂CHF₂,     CF₂CF₃, OCH₃, OCH₂CH₃, OCH₂OCH₃, OCH₂CH₂OCH₂CH₃, OCH₂OCH₂CH₃ or     OCH₂CH₂OCH₃, and in particular is H, F, Cl, CH₃, CF₃, OCH₃, OCH₂CH₃,     OCH₂OCH₃ or OCH₂CH₂OCH₃.

According to a particular embodiment of the invention the variable R² in the compounds of formula I is phenyl which is unsubstituted or carries one radical R²¹, where R²¹ is preferably attached to position 4 of the phenyl group and is as defined above and in particular selected from C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkyl and C₁-C₂-alkoxy-C₁-C₂-alkoxy, preferably form CH₃, C₂H₅, OCH₃, OC₂H₅, CHF₂, CF₃, OCH₂OCH₃ and OCH₂CH₂OCH₃, and specifically from OCH₃ and OC₂H₅.

According to a preferred embodiment of the invention the variable R² in the compounds of formula I is selected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and C₁-C₄-alkyl.

According to another preferred embodiment of the invention the variable R² in the compounds of formula I is selected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₃-alkoxy-C₁-C₃-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and C₁-C₄-alkyl.

According to another preferred embodiment of the invention the variable R² in the compounds of formula I is selected from the group consisting of halogen, C₁-C-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), where k is 0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from halogen and C₁-C₄-alkyl.

According to a more preferred embodiment of the invention the variable R² in the compounds of formula I is selected from C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy-C₁-C₂-alkyl, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy, C₁-C₄-alkoxycarbonyl and C₁-C₄-alkyl-S(O₂), and in particular from CH═CH₂, CH═CHCH₃, CH₂OCH₂CF₃, OC₂H₅, OCH₂CH═CH₂, OCH₂C≡CH, C(O)OCH₃, C(O)OC₂H₅, SO₂CH₃, SO₂C₂H₅ and SO₂CH(CH₃)₂.

According to a specifically preferred embodiment of the invention the variable R² in the compounds of formula I is selected from the group consisting of hydrogen, 4,5-dihydroisoxazol-3-yl, which is unsubstituted or substituted in position 5 with CH₃, CH₂F or CHF₂, 4,5-dihydroisoxazol-5-yl, which is unsubstituted or substituted in position 3 with CH₃, OCH₃, CH₂OCH₃, CH₂SCH₃, 1-methyl-5-oxo-1,5-dihydrotetrazol-2-yl, 4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl, morpholin-4-yl, isoxazol-3-yl, 5-methyl-isoxazol-3-yl, isoxazol-5-yl, 3-methyl-isoxazol-5-yl, 1-methyl-1H-pyrazol-3-yl, 2-methyl-2H-pyrazol-3-yl, thiazol-2-yl, 4-CH₃-phenyl, 4-C₂H⁵-phenyl, 4-OCH₃-phenyl, 4-OC₂H₅-phenyl, 4-CHF₂-phenyl, 4-CF₃-phenyl, 4-OCH₂OCH₃-phenyl, 4-OCH₂CH₂OCH₃-phenyl, CH═CH₂, CH═CHCH₃, CH₂OCH₂CF₃, OC₂H₅, OCH₂CH═CH₂, OCH₂C≡CH, C(O)OCH₃, C(O)OC₂H₅, SO₂CH₃, SO₂C₂H₅ and SO₂CH(CH₃)₂, in particular selected from hydrogen, halogen, methyl, CH₂OCH₂CF₃, methylsulfonyl, ethylsulfonyl, methylsulfanyl, ethylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 5-isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5-isoxazolyl, and specifically selected from hydrogen, chlorine, methylsulfonyl, methylsulfanyl, CH₂OCH₂CF₃, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl and 3-methyl-5-isoxazolyl.

Preferred compounds according to the invention are compounds of formula I, wherein R³ is selected from the group consisting of hydrogen, cyano, halogen, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₄-alkenyloxy, C₃-C₄-alkynyloxy or R^(2b)—S(O)_(k), where the variables k and R^(2b) have one of the herein defined meanings.

More preferably, R³ is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkyl-S(O)₂ and C₁-C₄-haloalkyl-S(O)₂.

In particular, R³ is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkylthio, C₁-C₂-haloalkylthio, C₁-C₂-alkyl-S(O)₂ and C₁-C₂-haloalkyl-S(O)₂, specifically from H, Cl, F, CN, NO₂, CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂, SCH₃, SCF₃, SCHF₂, S(O)₂CH₃ and S(O)₂CH₂CH₃, and more specifically from H, Cl, F, CN, CH₃, CF₃ and S(O)₂CH₃.

Preferred compounds according to the invention are compounds of formula I, wherein R⁴ is selected from the group consisting of hydrogen, cyano, halogen, nitro, C₁-C₂-alkyl and C₁-C₂-haloalkyl, in particular from the group consisting of hydrogen, CHF₂, CF₃, CN, NO₂, CH₃ and halogen, and specifically from hydrogen, CHF₂, CF₃, CN, NO₂, CH₃, Cl, Br and F.

Preferred compounds according to the invention are compounds of formula I, wherein R⁵ is selected from the group consisting of halogen, C₁-C₂-alkyl and C₁-C₂-haloalkyl, and in particular from the group consisting of CHF₂, CF₃ and halogen.

According to a particular embodiment of the invention R⁵ is chlorine or fluorine.

According to one embodiment of the invention, R⁶ in the compounds formula I is hydrogen.

According to another embodiment of the invention, R⁶ in the compounds formula I is selected from the group consisting of hydrogen, CN, C₁-C₆-alkyl, C₁-C₆-cyano-alkyl, C₁-C₆-alkoxy, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, R^(b)R^(b)N—S(O)_(n)—Z, R^(b)O—S(O)_(n)—Z, R^(b)—S(O)_(n)—Z, R^(d)—C(═O)O—C₁-C₃-alkyl, R^(d)—O—C(═O)O—C₁-C₃-alkyl, R^(d)O—C(═O)—C₁-C₃-alkyl, R^(e)R^(f)N—C(═O)—C₁-C₃-alkyl, phenyl-Z and where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 groups R′, which are identical or different.

Preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, R^(c)—C(═O)—C₁-C₂-alkyl, R^(d)O—C(═O)—C₁-C₂-alkyl, R^(e)R^(f)N—C(═O)—C₁-C₂-alkyl, R^(k)—C(═O)NH—C₁-C₂-alkyl and benzyl, where

R^(c) is C₁-C₄-alkyl or C₁-C₄-haloalkyl,

R^(d) is C₁-C₄-alkyl,

R^(e) is hydrogen or C₁-C₄-alkyl,

R^(f) is hydrogen or C₁-C₄-alkyl, or

R^(e), R^(f) together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 methyl groups,

R^(k) is C₁-C₄-alkyl.

Further preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, R^(d)O—C(═O)—C₁-C₃-alkyl, phenyl-Z and where phenyl is unsubstituted or substituted by 1, 2, 3 or 4 groups R′, which are identical or different.

Particularly preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and phenyl-C₁-C₂-alkyl, particularly from hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl.

Most preferred compounds according to the invention are compounds of formula I, wherein R⁶ is selected from the group consisting of hydrogen and C₁-C₄-alkyl, particularly from hydrogen, methyl and ethyl.

Preferred compounds according to the invention are compounds of formula I, wherein R⁷ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, R^(c)—C(═O)—C₁-C₂-alkyl, R^(d)O—C(═O)—C₁-C₂-alkyl, R^(e)R^(f)N—C(═O)—C₁-C₂-alkyl, R^(k)—C(═O)NH—C₁-C₂-alkyl and benzyl, where

R^(c) is C₁-C_(A)-alkyl or C₁-C₄-haloalkyl,

R^(d) is C₁-C₄-alkyl,

R^(e) is hydrogen or C₁-C₄-alkyl,

R^(f) is hydrogen or C₁-C₄-alkyl, or

R^(e), R^(f) together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 methyl groups,

R^(k) is C₁-C₄-alkyl.

Further preferred compounds according to the invention are compounds of formula I, wherein

-   -   R⁷ is selected from the group consisting of C₁-C₄-alkyl,         C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₄-alkoxy and C₁-C₄-alkoxy-C₁-C₄-alkyl.

Particularly preferred compounds according to the invention are compounds of formula I, wherein R⁷ is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₂-alkoxy-C₁-C₂-alkyl, particularly from methyl, ethyl, methoxy, ethoxy, n-propyl, methoxymethyl, ethoxymethyl and methoxyethyl.

Most preferred compounds according to the invention are compounds of formula I, wherein R⁷ is selected from the group consisting methyl, ethyl, n-propyl and methoxyethyl.

In this context, the variables R′, R¹¹, R²¹, Z, Z¹, Z², Z^(2a), R^(b), R^(1b), R^(2b), R^(c), R^(2c), R^(d), R^(2d), R^(e), R^(2e), R^(f), R^(2f), R^(g), R^(2g), R^(h), R^(2h), R^(k), n and k, independently of each other, preferably have one of the following meanings:

R′, R¹¹, R²¹ independently of each other are selected from halogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-halocycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy and C₁-C₆-haloalkyloxy, more preferably from halogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy.

More preferably R′, R¹¹, R²¹ independently of each other are selected from the group consisting of halogen, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkoxy; in particular selected from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkoxy-C₁-C₄-alkoxy; and specifically from Cl, F, Br, methyl, ethyl, methoxy and trifluoromethyl.

Z, Z¹, Z² independently of each other are selected from a covalent bond, methanediyl and ethanediyl, and in particular are a covalent bond.

Z^(2a) is selected from a covalent bond, C₁-C₂-alkanediyl, O—C₁-C₂-alkanediyl, C₁-C₂-alkanediyl-O and C₁-C₂-alkanediyl-O—C₁-C₂-alkanediyl; more preferably from a covalent bond, methanediyl, ethanediyl, O-methanediyl, O-ethanediyl, methanediyl-O, and ethanediyl-O; and in particular from a covalent bond, methanediyl and ethanediyl.

R^(b), R^(1b), R^(2b) independently of each other are selected from C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₇-haloalkyl and C₁-C₂-alkoxy.

More preferably R^(b), R^(1b), R^(2b) independently of each other are selected from the group consisting of C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.

In particular, R^(b), R^(1b), R^(2b) independently of each other are selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.

R^(c), R^(2C), R^(k) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partly or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S, where phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy.

More preferably R^(c), R^(2c), R^(k) independently of each other are selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C-alkenyl, C₂-C-haloalkenyl, C₂-C-alkynyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2 or 3 heteroatoms as ring members, which are selected from the group consisting of O, N and S.

In particular, R^(c), R^(2c), R^(k) independently of each other are selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₃-C₆-cycloalkyl, phenyl and heterocyclyl, where heterocyclyl is a 5- or 6-membered aromatic heterocyclic radical having 1 or 2 nitrogen atoms as ring members.

R^(d), R^(2d) independently of each other are selected from C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partly or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl.

More preferably R^(d), R^(2d) independently of each other are selected from C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, C₂-C₄-alkynyl and C₃-C₆-cycloalkyl.

R^(e), R^(f), R^(2e), R^(2f) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, where phenyl and benzyl are unsubstituted or substituted by 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy, or R^(e) and R^(f) or R^(2e) and R^(2f) together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy.

More preferably R^(e), R^(f), R^(2e), R^(2f) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl and benzyl, or R^(e) and R^(f) or R^(2e) and R^(2f) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl.

In particular, R^(e), R^(f), R^(2e), R^(2f) independently of each other are selected from hydrogen and C₁-C₄-alkyl, or R^(e) and R^(f) or R^(2e) and R^(2f) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 methyl groups.

R^(g), R^(2g) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partly or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl and benzyl.

More preferably R^(g), R^(2g) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, benzyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, benzyl and C₃-C₆-cycloalkyl.

R^(h), R^(2h) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, which is unsubstituted or partly or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl, benzyl and a radical C(═O)—R^(k), where R^(k) is H, C₁-C₄-alkyl, C₁-C₄-haloalkyl or phenyl.

More preferably R^(h), R^(2h) independently of each other are selected from hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, benzyl, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₃-C₇-cycloalkyl, which is unsubstituted or partly or completely halogenated, and in particular selected from hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₂-C₄-alkenyl, C₂-C₄-haloalkenyl, benzyl and C₃-C₆-cycloalkyl; or

R^(g) and R^(h) or R^(2g) and R^(2h) together with the nitrogen atom, to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of ═O, halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl and C₁-C₄-alkoxy;

more preferably R^(g) and R^(h) or R^(2q) and R^(2h) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-haloalkyl;

and in particular, R^(g) and R^(h) or R^(2g) and R^(2h) together with the nitrogen atom, to which they are bound may form a 5- or 6-membered, saturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from O, S and N and which is unsubstituted or may carry 1, 2 or 3 methyl groups.

n and k independently of each other are 0 or 2, and in particular 2.

Particularly preferred are compounds of formula I, wherein the variables R¹ and R³ have the following meanings:

R¹ is selected from the group consisting of halogen, nitro, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and C₁-C₄-alkylsulfonyl, in particular from F, Cl, Br, NO₂, CH₃, cyclopropyl, CF₃, OCH₃, SCH₃, OCF₃, SCF₃, SO₂CH₃, CH₂OCH₃ and CH₂OCH₂CH₂OCH₃; and

R³ is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and C₁-C₄-alkylsulfonyl, in particular from H, Cl, F, CN, NO₂, CH₃, CF₃, CHF₂, OCH₃, OCF₃, OCHF₂, SCH₃, SCF₃, SCHF₂, S(O)₂CH₃ and S(O)₂CH₂CH₃.

Especially preferred are compounds of formula I, where X is CR² and the variables R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings:

-   -   R¹ is selected from the group consisting of halogen, nitro,         cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl         and C₁-C₄-alkyl-S(O)₂;     -   R² is selected from the group consisting of hydrogen, halogen,         C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,         C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₄-alkoxy, C₁-C₃-alkoxy-C₁-C₃-alkoxy, C₁-C₄-haloalkoxy,         C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy,         C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkyl-S(O)_(k)         and C₁-C₄-haloalkyl-S(O)_(k), where k is 0, 1 or 2, isoxazolyl         and isoxazolinyl, where the last two mentioned radicals may be         unsubstituted or carry 1 or 2 radicals selected from halogen and         C₁-C₄-alkyl;     -   R³ is selected from the group consisting of hydrogen, halogen,         CN, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂;     -   R⁴ is selected from the group consisting of hydrogen and         halogen;     -   R⁵ is selected from the group consisting of halogen, CHF₂ and         CF₃;     -   R⁶ is selected from the group consisting of hydrogen,         C₁-C₄-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₂-C₄-alkenyl,         C₂-C₄-alkynyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and         phenyl-C₁-C₂-alkyl;     -   R⁷ is selected from the group consisting of C₁-C₄-alkyl,         C₁-C₄-alkoxy and C₁-C₂-alkoxy-C₁-C₂-alkyl.

Also especially preferred are compounds of formula I, where X is CR² and the variables R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings:

-   -   R¹ is selected from the group consisting of halogen, nitro,         cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl         and C₁-C₄-alkyl-S(O)₂;     -   R² is selected from the group consisting of hydrogen, halogen,         C₁-C₄-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl,         C₁-C₂-haloalkoxy-C₁-C₂-alkyl, C₁-C₄-alkyl-S(O)_(k), where k is         0, 1 or 2, isoxazolyl and isoxazolinyl, where the last two         mentioned radicals may be unsubstituted or carry 1 or 2 radicals         selected from halogen and C₁-C₄-alkyl;     -   R³ is selected from the group consisting of hydrogen, halogen,         CN, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂;     -   R⁴ is selected from the group consisting of hydrogen and         halogen;     -   R⁵ is selected from the group consisting of halogen, CHF₂ and         CF₃;     -   R⁶ is selected from the group consisting of hydrogen,         C₁-C₄-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₂-C₄-alkenyl,         C₂-C₄-alkynyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and         phenyl-C₁-C₂-alkyl;     -   R⁷ is selected from the group consisting of C₁-C₄-alkyl,         C₁-C₄-alkoxy and C₁-C₂-alkoxy-C₁-C₂-alkyl.

Specifically preferred are compounds of formula I, where X is CR² and the variables R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings:

-   -   R¹ is selected from the group consisting of chlorine, nitro,         methyl, trifluoromethyl and methylsulfonyl;     -   R² is selected from the group consisting of hydrogen, chlorine,         fluorine, methyl, methyl-sulfonyl, methylsulfinyl,         methylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl,         5-isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl,         5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5-isoxazolyl;     -   R³ is selected from the group consisting of hydrogen, fluorine,         chlorine, CN, trifluoromethyl, and methylsulfonyl;     -   R⁴ is selected from the group consisting of hydrogen, chlorine         and fluorine; R⁵ is selected from the group consisting of         chlorine and fluorine;     -   R⁶ is selected from the group consisting of hydrogen, methyl,         ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl,         methoxycarbonylmethyl and benzyl;     -   R⁷ is selected from the group consisting of methyl, ethyl,         methoxy, ethoxy, methoxymethyl, methoxyethyl and ethoxymethyl;

Especially preferred are compounds of formula I, where X is N and the variables R¹, R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings:

-   -   R¹ is selected from the group consisting of halogen, nitro,         cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl,         C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl         and C₁-C₄-alkyl-S(O)₂;     -   R³ is selected from the group consisting of hydrogen, halogen,         CN, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂;     -   R⁴ is selected from the group consisting of hydrogen and         halogen;     -   R⁵ is selected from the group consisting of halogen, CHF₂ and         CF₃;     -   R⁶ is selected from the group consisting of hydrogen,         C₁-C₄-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₂-C₄-alkenyl,         C₂-C₄-alkynyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and         phenyl-C₁-C₂-alkyl;     -   R⁷ is selected from the group consisting of C₁-C₄-alkyl,         C₁-C₄-alkoxy and C₁-C₂-alkoxy-C₁-C₂-alkyl.

Also specifically preferred are compounds of formula I, where X is N and the variables R¹, R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings:

-   -   R¹ is selected from the group consisting of chlorine, nitro,         methyl, trifluoromethyl and methylsulfonyl;     -   R³ is selected from the group consisting of hydrogen, fluorine,         chlorine, CN, trifluoromethyl, and methylsulfonyl;     -   R⁴ is selected from the group consisting of hydrogen, chlorine         and fluorine;     -   R⁵ is selected from the group consisting of chlorine and         fluorine;     -   R⁶ is selected from the group consisting of hydrogen, methyl,         ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl,         methoxycarbonylmethyl and benzyl;     -   R⁷ is selected from the group consisting of methyl, ethyl,         methoxy, ethoxy, methoxymethyl, methoxyethyl and ethoxymethyl;

According to another preferred embodiment of the invention, where X is CR², the variables R¹, R², R³, R⁴ and R⁵ together form one of the following substitution patterns on the phenyl ring of compounds of formula I, provided that position 1 is the attachment point of the phenyl ring to the remainder of the molecule: 2-Br-4,6-Cl₂, 2,6-Cl₂-4-CN, 2,4,6-Cl₃, 2,6-Cl₂-4-F, 2,6-Cl₂-4-CF₃, 2,6-Cl₂-4-S(O)₂CH₃, 2-CF₃-4-CN-6-Cl, 2-CF₃-4,6-Cl₂, 2-CF₃-4-CF₃-6-Cl, 2-CF₃-4-S(O)₂CH₃-6-Cl, 2-CF₃-4-F-6-Cl, 2-CH₃—CN-6-Cl, 2-CH₃-4,6-Cl₂, 2-CH₃-4-CF₃-6-Cl, 2-CH₃-4-S(O)₂CH₃-6-Cl, 2-CH₃-4-F-6-Cl, 2-S(O)₂CH₃-4-CN-6-Cl, 2-S(O)₂CH₃-4,6-Cl₂, 2-S(O)₂CH₃-4-CF₃-6-Cl, 2-S(O)₂CH₃-4-S(O)₂CH₃-6-Cl, 2-S(O)₂CH₃-4-F-6-Cl, 2-Cl-4-CN-6-F, 2-Cl-4-CF₃-6-F, 2-Cl-4-S(O)₂CH₃-6-F, 2,4-Cl₂-6-F, 2-Cl-4,6-F₂, 2-CF₃-4-CN-6-F, 2-CF₃-4-CF₃-6-F, 2-CF₃-4-S(O)₂CH₃-6-F, 2-CF₃-4-Cl-6-F, 2-CF₃-4,6-F₂, 2-CH₃-4-CN-6-F, 2-CH₃-4-CF₃-6-F, 2-CH₃-4-S(O)₂CH₃-6-F, 2-CH₃-4-Cl-6-F, 2-CH₃-4,6-F₂, 2-S(O)₂CH₃-4-CN-6-F, 2-S(O)₂CH₃-4-CF₃-6-F, 2-S(O)₂CH₃-4-S(O)₂CH₃-6-F, 2-S(O)₂CH₃-4-Cl-6-F, 2-S(O)₂CH₃-4,6-F₂, 2,5-Cl₂-4-CN, 2,4,5- Cl₃, 2,5-Cl₂-4-F, 2,5-Cl₂-4-CF₃, 2,5-Cl₂-4-S(O)₂CH₃, 2-CF₃-4-CN-5-Cl, 2-CF₃-4,5-Cl₂, 2-CF₃-4-CF₃-5-Cl, 2-CF₃-4-S(O)₂CH₃-5-Cl, 2-CF₃-4-F-5-Cl, 2-CH₃-4-CN-5-Cl, 2-CH₃-4,5-Cl₂, 2-CH₃-4-CF₃-5-Cl, 2-CH₃-4-S(O)₂CH₃-5-Cl, 2-CH₃-4-F-5-Cl, 2-S(O)₂CH₃-4-CN-5-Cl, 2-S(O)₂CH₃-4,5-Cl₂, 2-S(O)₂CH₃-4-CF₃-5-Cl, 2-S(O)₂CH₃-4-S(O)₂CH₃-5-Cl, 2-S(O)₂CH₃-4-F-5-Cl, 2-Cl-4-CN-5-F, 2-Cl-4-CF₃-5-F, 2-Cl-4-S(O)₂CH₃-5-F, 2,4-Cl₂-5-F, 2-Cl-4,5-F₂, 2-CF₃-4-CN-5-F, 2-CF₃-4-CF₃-5-F, 2-CF₃-4-S(O)₂CH₃-5-F, 2-CF₃-4-Cl-5-F, 2-CF₃-4,5-F₂, 2-CH₃-4-CN-5-F, 2-CH₃-4-CF₃-5-F, 2-CH₃-4-S(O)₂CH₃-5-F, 2-CH₃-4-Cl-5-F, 2-CH₃-4,5-F₂, 2-S(O)₂CH₃-4-CN-5-F, 2-S(O)₂CH₃-4-CF₃-5-F, 2-S(O)₂CH₃-4-S(O)₂CH₃-5-F, 2-S(O)₂CH₃-4-Cl-5-F or 2-S(O)₂CH₃-4,5-F₂.

According to another preferred embodiment of the invention the variables R¹, R², R³, R⁴ and R⁵ together form one of the following substitution patterns on the phenyl ring of compounds of formula I, provided that position 1 is the attachment point of the phenyl ring to the remainder of the molecule:

2,6-Cl₂-3-(3-isoxazolinyl)-4-CN, 2,4,6-Cl₃-3-(3-isoxazolinyl), 2,6-Cl₂-3-(3-isoxazolinyl)-4-F, 2,6-Cl₂-3-(3-isoxazolinyl)-4-CF₃, 2,6-Cl₂-3-(3-isoxazolinyl)-4-S(O)₂CH₃, 2-CF₃-3-(3-isoxazolinyl)-4-CN-6-Cl, 2-CF₃-3-(3-isoxazolinyl)-4,6-Cl₂, 2-CF₃-3-(3-isoxazolinyl)-4-CF₃-6-Cl, 2-CF₃-3-(3-isoxazolinyl)-4-S(O)₂CH₃-6-Cl, 2-CF₃-3-(3-isoxazolinyl)-4-F-6-Cl, 2-CH₃-3-(3-isoxazolinyl)-4-CN-6-Cl, 2-CH₃-3-(3-isoxazolinyl)-4,6-Cl₂, 2-CH₃-3-(3-isoxazolinyl)-4-CF₃-6-Cl, 2-CH₃-3-(3-isoxazolinyl)-4-S(O)₂CH₃-6-Cl, 2-CH₃-3-(3-isoxazolinyl)-4-F-6-Cl, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-CN-6-Cl, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4,6-Cl₂, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-CF₃-6-Cl, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-S(O)₂CH₃-6-Cl, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-F-6-Cl, 2-Cl-3-(3-isoxazolinyl)-4-CN-6-F, 2-Cl-3-(3-isoxazolinyl)-4-CF₃-6-F, 2-Cl-3-(3-isoxazolinyl)-4-S(O)₂CH₃-6-F, 2,4-Cl₂-3-(3-isoxazolinyl)-6-F, 2-Cl-3-(3-isoxazolinyl)-4,6-F₂, 2-CF₃-3-(3-isoxazolinyl)-4-CN-6-F, 2-CF₃-3-(3-isoxazolinyl)-4-CF₃-6-F, 2-CF₃-3-(3-isoxazolinyl)-4-S(O)₂CH₃-6-F, 2-CF₃-3-(3-isoxazolinyl)-4-Cl-6-F, 2-CF₃-3-(3-isoxazolinyl)-4,6-F₂, 2-CH₃-3-(3-isoxazolinyl)-4-CN-6-F, 2-CH₃-3-(3-isoxazolinyl)-4-CF₃-6-F, 2-CH₃-3-(3-isoxazolinyl)-4-S(O)₂CH₃-6-F, 2-CH₃-3-(3-isoxazolinyl)-4-Cl-6-F, 2-CH₃-3-(3-isoxazolinyl)-4,6-F₂, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-CN-6-F, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-CF₃-6-F, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-S(O)₂CH₃-6-F, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4-Cl-6-F, 2-S(O)₂CH₃-3-(3-isoxazolinyl)-4,6-F₂, 2,5-Cl₂-3-(3-isoxazolinyl)-4-CN, 2,6-Cl₂-3-(CH₂—O—CH₂CF₃)-4-CN, 2,4,6-Cl₃-3-(3-isoxazolinyl), 2,6-Cl₂-3-(CH₂—O—CH₂CF₃)-4-F, 2,6-Cl₂-3-(CH₂—O—CH₂CF₃)-4-CF₃, 2,6-Cl₂-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-CN-6-Cl, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4,6-Cl₂, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-CF₃-6-Cl, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃-6-Cl, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-F-6-Cl, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-CN-6-Cl, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4,6-Cl₂, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-CF₃-6-Cl, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃-6-Cl, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-F-6-Cl, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-CN-6-Cl, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4,6-Cl₂, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-CF₃-6-Cl, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃-6-Cl, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-F-6-Cl, 2-Cl-3-(CH₂—O—CH₂CF₃)-4-CN-6-F, 2-Cl-3-(CH₂—O—CH₂CF₃)-4-CF₃-6-F, 2-Cl-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃-6-F, 2,4-Cl₂-3-(CH₂—O—CH₂CF₃)-6-F, 2-Cl-3-(CH₂—O—CH₂CF₃)-4,6-F₂, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-CN-6-F, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-CF₃-6-F, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃-6-F, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4-Cl-6-F, 2-CF₃-3-(CH₂—O—CH₂CF₃)-4,6-F₂, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-CN-6-F, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-CF₃-6-F, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃-6-F, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4-Cl-6-F, 2-CH₃-3-(CH₂—O—CH₂CF₃)-4,6-F₂, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-CN-6-F, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-CF₃-6-F, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-S(O)₂CH₃-6-F, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4-Cl-6-F, 2-S(O)₂CH₃-3-(CH₂—O—CH₂CF₃)-4,6-F₂,

Examples of preferred compounds I.A, where X is N, are the individual compounds compiled in Tables 1 to 15 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 1 Compounds of formula LA (I.A-1.1-I.A-1.2048) in which R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 2 Compounds of formula I.A (I.A-2.1-II.A-2.2048) in which R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 3 Compounds of formula I.A (I.A-3.1-I.A-3.2048) in which R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 4 Compounds of formula I.A (I.A-4.1-I.A-4.2048) in which R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 5 Compounds of formula I.A (I.A-5.1-I.A-5.2048) in which R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 6 Compounds of formula I.A (I.A-6.1-I.A-6.2048) in which R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 7 Compounds of formula I.A (I.A-7.1-I.A-7.2048) in which R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 8 Compounds of formula I.A (I.A-8.1-I.A-8.2048) in which R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 9 Compounds of formula I.A (I.A-9.1-I.A-9.2048) in which R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 10 Compounds of formula I.A (I.A-10.1-I.A-10.2048) in which R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 11 Compounds of formula I.A (I.A-11.1-I.A-11.2048) in which R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 12 Compounds of formula I.A (I.A-12.1-I.A-12.2048) in which R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 13 Compounds of formula I.A (I.A-13.1-I.A-13.2048) in which R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 14 Compounds of formula I.A (I.A-14.1-I.A-14.2048) in which R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 15 Compounds of formula I.A (I.A-15.1-I.A-15.2048) in which R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A;

TABLE A R¹ R³ R⁶ R⁷ A-1 Cl H CH₃ CH₃ A-2 Cl H CH₃ CH₂CH₃ A-3 Cl H CH₃ CH₂CH₂CH₃ A-4 Cl H CH₃ CH₂CH₂OCH₃ A-5 Cl H CH₂CH₃ CH₃ A-6 Cl H CH₂CH₃ CH₂CH₃ A-7 Cl H CH₂CH₃ CH₂CH₂CH₃ A-8 Cl H CH₂CH₃ CH₂CH₂OCH₃ A-9 Cl H CH₂OCH₃ CH₃ A-10 Cl H CH₂OCH₃ CH₂CH₃ A-11 Cl H CH₂OCH₃ CH₂CH₂CH₃ A-12 Cl H CH₂OCH₃ CH₂CH₂OCH₃ A-13 Cl H CH₂OCH₂CH₃ CH₃ A-14 Cl H CH₂OCH₂CH₃ CH₂CH₃ A-15 Cl H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-16 Cl H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-17 Cl H CH₂(CO)OCH₃ CH₃ A-18 Cl H CH₂(CO)OCH₃ CH₂CH₃ A-19 Cl H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-20 Cl H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-21 Cl H CH₂CHCH₂ CH₃ A-22 Cl H CH₂CHCH₂ CH₂CH₃ A-23 Cl H CH₂CHCH₂ CH₂CH₂CH₃ A-24 Cl H CH₂CHCH₂ CH₂CH₂OCH₃ A-25 Cl H CH₂CCH CH₃ A-26 Cl H CH₂CCH CH₂CH₃ A-27 Cl H CH₂CCH CH₂CH₂CH₃ A-28 Cl H CH₂CCH CH₂CH₂OCH₃ A-29 Cl H H CH₃ A-30 Cl H H CH₂CH₃ A-31 Cl H H CH₂CH₂CH₃ A-32 Cl H H CH₂CH₂OCH₃ A-33 Cl F CH₃ CH₃ A-34 Cl F CH₃ CH₂CH₃ A-35 Cl F CH₃ CH₂CH₂CH₃ A-36 Cl F CH₃ CH₂CH₂OCH₃ A-37 Cl F CH₂CH₃ CH₃ A-38 Cl F CH₂CH₃ CH₂CH₃ A-39 Cl F CH₂CH₃ CH₂CH₂CH₃ A-40 Cl F CH₂CH₃ CH₂CH₂OCH₃ A-41 Cl F CH₂OCH₃ CH₃ A-42 Cl F CH₂OCH₃ CH₂CH₃ A-43 Cl F CH₂OCH₃ CH₂CH₂CH₃ A-44 Cl F CH₂OCH₃ CH₂CH₂OCH₃ A-45 Cl F CH₂OCH₂CH₃ CH₃ A-46 Cl F CH₂OCH₂CH₃ CH₂CH₃ A-47 Cl F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-48 Cl F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-49 Cl F CH₂(CO)OCH₃ CH₃ A-50 Cl F CH₂(CO)OCH₃ CH₂CH₃ A-51 Cl F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-52 Cl F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-53 Cl F CH₂CHCH₂ CH₃ A-54 Cl F CH₂CHCH₂ CH₂CH₃ A-55 Cl F CH₂CHCH₂ CH₂CH₂CH₃ A-56 Cl F CH₂CHCH₂ CH₂CH₂OCH₃ A-57 Cl F CH₂CCH CH₃ A-58 Cl F CH₂CCH CH₂CH₃ A-59 Cl F CH₂CCH CH₂CH₂CH₃ A-60 Cl F CH₂CCH CH₂CH₂OCH₃ A-61 Cl F H CH₃ A-62 Cl F H CH₂CH₃ A-63 Cl F H CH₂CH₂CH₃ A-64 Cl F H CH₂CH₂OCH₃ A-65 Cl Cl CH₃ CH₃ A-66 Cl Cl CH₃ CH₂CH₃ A-67 Cl Cl CH₃ CH₂CH₂CH₃ A-68 Cl Cl CH₃ CH₂CH₂OCH₃ A-69 Cl Cl CH₂CH₃ CH₃ A-70 Cl Cl CH₂CH₃ CH₂CH₃ A-71 Cl Cl CH₂CH₃ CH₂CH₂CH₃ A-72 Cl Cl CH₂CH₃ CH₂CH₂OCH₃ A-73 Cl Cl CH₂OCH₃ CH₃ A-74 Cl Cl CH₂OCH₃ CH₂CH₃ A-75 Cl Cl CH₂OCH₃ CH₂CH₂CH₃ A-76 Cl Cl CH₂OCH₃ CH₂CH₂OCH₃ A-77 Cl Cl CH₂OCH₂CH₃ CH₃ A-78 Cl Cl CH₂OCH₂CH₃ CH₂CH₃ A-79 Cl Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-80 Cl Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-81 Cl Cl CH₂(CO)OCH₃ CH₃ A-82 Cl Cl CH₂(CO)OCH₃ CH₂CH₃ A-83 Cl Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-84 Cl Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-85 Cl Cl CH₂CHCH₂ CH₃ A-86 Cl Cl CH₂CHCH₂ CH₂CH₃ A-87 Cl Cl CH₂CHCH₂ CH₂CH₂CH₃ A-88 Cl Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-89 Cl Cl CH₂CCH CH₃ A-90 Cl Cl CH₂CCH CH₂CH₃ A-91 Cl Cl CH₂CCH CH₂CH₂CH₃ A-92 Cl Cl CH₂CCH CH₂CH₂OCH₃ A-93 Cl Cl H CH₃ A-94 Cl Cl H CH₂CH₃ A-95 Cl Cl H CH₂CH₂CH₃ A-96 Cl Cl H CH₂CH₂OCH₃ A-97 Cl Br CH₃ CH₃ A-98 Cl Br CH₃ CH₂CH₃ A-99 Cl Br CH₃ CH₂CH₂CH₃ A-100 Cl Br CH₃ CH₂CH₂OCH₃ A-101 Cl Br CH₂CH₃ CH₃ A-102 Cl Br CH₂CH₃ CH₂CH₃ A-103 Cl Br CH₂CH₃ CH₂CH₂CH₃ A-104 Cl Br CH₂CH₃ CH₂CH₂OCH₃ A-105 Cl Br CH₂OCH₃ CH₃ A-106 Cl Br CH₂OCH₃ CH₂CH₃ A-107 Cl Br CH₂OCH₃ CH₂CH₂CH₃ A-108 Cl Br CH₂OCH₃ CH₂CH₂OCH₃ A-109 Cl Br CH₂OCH₂CH₃ CH₃ A-110 Cl Br CH₂OCH₂CH₃ CH₂CH₃ A-111 Cl Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-112 Cl Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-113 Cl Br CH₂(CO)OCH₃ CH₃ A-114 Cl Br CH₂(CO)OCH₃ CH₂CH₃ A-115 Cl Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-116 Cl Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-117 Cl Br CH₂CHCH₂ CH₃ A-118 Cl Br CH₂CHCH₂ CH₂CH₃ A-119 Cl Br CH₂CHCH₂ CH₂CH₂CH₃ A-120 Cl Br CH₂CHCH₂ CH₂CH₂OCH₃ A-121 Cl Br CH₂CCH CH₃ A-122 Cl Br CH₂CCH CH₂CH₃ A-123 Cl Br CH₂CCH CH₂CH₂CH₃ A-124 Cl Br CH₂CCH CH₂CH₂OCH₃ A-125 Cl Br H CH₃ A-126 Cl Br H CH₂CH₃ A-127 Cl Br H CH₂CH₂CH₃ A-128 Cl Br H CH₂CH₂OCH₃ A-129 Cl CN CH₃ CH₃ A-130 Cl CN CH₃ CH₂CH₃ A-131 Cl CN CH₃ CH₂CH₂CH₃ A-132 Cl CN CH₃ CH₂CH₂OCH₃ A-133 Cl CN CH₂CH₃ CH₃ A-134 Cl CN CH₂CH₃ CH₂CH₃ A-135 Cl CN CH₂CH₃ CH₂CH₂CH₃ A-136 Cl CN CH₂CH₃ CH₂CH₂OCH₃ A-137 Cl CN CH₂OCH₃ CH₃ A-138 Cl CN CH₂OCH₃ CH₂CH₃ A-139 Cl CN CH₂OCH₃ CH₂CH₂CH₃ A-140 Cl CN CH₂OCH₃ CH₂CH₂OCH₃ A-141 Cl CN CH₂OCH₂CH₃ CH₃ A-142 Cl CN CH₂OCH₂CH₃ CH₂CH₃ A-143 Cl CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-144 Cl CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-145 Cl CN CH₂(CO)OCH₃ CH₃ A-146 Cl CN CH₂(CO)OCH₃ CH₂CH₃ A-147 Cl CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-148 Cl CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-149 Cl CN CH₂CHCH₂ CH₃ A-150 Cl CN CH₂CHCH₂ CH₂CH₃ A-151 Cl CN CH₂CHCH₂ CH₂CH₂CH₃ A-152 Cl CN CH₂CHCH₂ CH₂CH₂OCH₃ A-153 Cl CN CH₂CCH CH₃ A-154 Cl CN CH₂CCH CH₂CH₃ A-155 Cl CN CH₂CCH CH₂CH₂CH₃ A-156 Cl CN CH₂CCH CH₂CH₂OCH₃ A-157 Cl CN H CH₃ A-158 Cl CN H CH₂CH₃ A-159 Cl CN H CH₂CH₂CH₃ A-160 Cl CN H CH₂CH₂OCH₃ A-161 Cl CH₃ CH₃ CH₃ A-162 Cl CH₃ CH₃ CH₂CH₃ A-163 Cl CH₃ CH₃ CH₂CH₂CH₃ A-164 Cl CH₃ CH₃ CH₂CH₂OCH₃ A-165 Cl CH₃ CH₂CH₃ CH₃ A-166 Cl CH₃ CH₂CH₃ CH₂CH₃ A-167 Cl CH₃ CH₂CH₃ CH₂CH₂CH₃ A-168 Cl CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-169 Cl CH₃ CH₂OCH₃ CH₃ A-170 Cl CH₃ CH₂OCH₃ CH₂CH₃ A-171 Cl CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-172 Cl CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-173 Cl CH₃ CH₂OCH₂CH₃ CH₃ A-174 Cl CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-175 Cl CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-176 Cl CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-177 Cl CH₃ CH₂(CO)OCH₃ CH₃ A-178 Cl CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-179 Cl CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-180 Cl CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-181 Cl CH₃ CH₂CHCH₂ CH₃ A-182 Cl CH₃ CH₂CHCH₂ CH₂CH₃ A-183 Cl CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-184 Cl CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-185 Cl CH₃ CH₂CCH CH₃ A-186 Cl CH₃ CH₂CCH CH₂CH₃ A-187 Cl CH₃ CH₂CCH CH₂CH₂CH₃ A-188 Cl CH₃ CH₂CCH CH₂CH₂OCH₃ A-189 Cl CH₃ H CH₃ A-190 Cl CH₃ H CH₂CH₃ A-191 Cl CH₃ H CH₂CH₂CH₃ A-192 Cl CH₃ H CH₂CH₂OCH₃ A-193 Cl CF₃ CH₃ CH₃ A-194 Cl CF₃ CH₃ CH₂CH₃ A-195 Cl CF₃ CH₃ CH₂CH₂CH₃ A-196 Cl CF₃ CH₃ CH₂CH₂OCH₃ A-197 Cl CF₃ CH₂CH₃ CH₃ A-198 Cl CF₃ CH₂CH₃ CH₂CH₃ A-199 Cl CF₃ CH₂CH₃ CH₂CH₂CH₃ A-200 Cl CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-201 Cl CF₃ CH₂OCH₃ CH₃ A-202 Cl CF₃ CH₂OCH₃ CH₂CH₃ A-203 Cl CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-204 Cl CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-205 Cl CF₃ CH₂OCH₂CH₃ CH₃ A-206 Cl CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-207 Cl CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-208 Cl CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-209 Cl CF₃ CH₂(CO)OCH₃ CH₃ A-210 Cl CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-211 Cl CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-212 Cl CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-213 Cl CF₃ CH₂CHCH₂ CH₃ A-214 Cl CF₃ CH₂CHCH₂ CH₂CH₃ A-215 Cl CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-216 Cl CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-217 Cl CF₃ CH₂CCH CH₃ A-218 Cl CF₃ CH₂CCH CH₂CH₃ A-219 Cl CF₃ CH₂CCH CH₂CH₂CH₃ A-220 Cl CF₃ CH₂CCH CH₂CH₂OCH₃ A-221 Cl CF₃ H CH₃ A-222 Cl CF₃ H CH₂CH₃ A-223 Cl CF₃ H CH₂CH₂CH₃ A-224 Cl CF₃ H CH₂CH₂OCH₃ A-225 Cl SO₂CH₃ CH₃ CH₃ A-226 Cl SO₂CH₃ CH₃ CH₂CH₃ A-227 Cl SO₂CH₃ CH₃ CH₂CH₂CH₃ A-228 Cl SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-229 Cl SO₂CH₃ CH₂CH₃ CH₃ A-230 Cl SO₂CH₃ CH₂CH₃ CH₂CH₃ A-231 Cl SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-232 Cl SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-233 Cl SO₂CH₃ CH₂OCH₃ CH₃ A-234 Cl SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-235 Cl SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-236 Cl SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-237 Cl SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-238 Cl SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-239 Cl SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-240 Cl SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-241 Cl SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-242 Cl SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-243 Cl SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-244 Cl SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-245 Cl SO₂CH₃ CH₂CHCH₂ CH₃ A-246 Cl SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-247 Cl SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-248 Cl SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-249 Cl SO₂CH₃ CH₂CCH CH₃ A-250 Cl SO₂CH₃ CH₂CCH CH₂CH₃ A-251 Cl SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-252 Cl SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-253 Cl SO₂CH₃ H CH₃ A-254 Cl SO₂CH₃ H CH₂CH₃ A-255 Cl SO₂CH₃ H CH₂CH₂CH₃ A-256 Cl SO₂CH₃ H CH₂CH₂OCH₃ A-257 NO₂ H CH₃ CH₃ A-258 NO₂ H CH₃ CH₂CH₃ A-259 NO₂ H CH₃ CH₂CH₂CH₃ A-260 NO₂ H CH₃ CH₂CH₂OCH₃ A-261 NO₂ H CH₂CH₃ CH₃ A-262 NO₂ H CH₂CH₃ CH₂CH₃ A-263 NO₂ H CH₂CH₃ CH₂CH₂CH₃ A-264 NO₂ H CH₂CH₃ CH₂CH₂OCH₃ A-265 NO₂ H CH₂OCH₃ CH₃ A-266 NO₂ H CH₂OCH₃ CH₂CH₃ A-267 NO₂ H CH₂OCH₃ CH₂CH₂CH₃ A-268 NO₂ H CH₂OCH₃ CH₂CH₂OCH₃ A-269 NO₂ H CH₂OCH₂CH₃ CH₃ A-270 NO₂ H CH₂OCH₂CH₃ CH₂CH₃ A-271 NO₂ H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-272 NO₂ H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-273 NO₂ H CH₂(CO)OCH₃ CH₃ A-274 NO₂ H CH₂(CO)OCH₃ CH₂CH₃ A-275 NO₂ H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-276 NO₂ H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-277 NO₂ H CH₂CHCH₂ CH₃ A-278 NO₂ H CH₂CHCH₂ CH₂CH₃ A-279 NO₂ H CH₂CHCH₂ CH₂CH₂CH₃ A-280 NO₂ H CH₂CHCH₂ CH₂CH₂OCH₃ A-281 NO₂ H CH₂CCH CH₃ A-282 NO₂ H CH₂CCH CH₂CH₃ A-283 NO₂ H CH₂CCH CH₂CH₂CH₃ A-284 NO₂ H CH₂CCH CH₂CH₂OCH₃ A-285 NO₂ H H CH₃ A-286 NO₂ H H CH₂CH₃ A-287 NO₂ H H CH₂CH₂CH₃ A-288 NO₂ H H CH₂CH₂OCH₃ A-289 NO₂ F CH₃ CH₃ A-290 NO₂ F CH₃ CH₂CH₃ A-291 NO₂ F CH₃ CH₂CH₂CH₃ A-292 NO₂ F CH₃ CH₂CH₂OCH₃ A-293 NO₂ F CH₂CH₃ CH₃ A-294 NO₂ F CH₂CH₃ CH₂CH₃ A-295 NO₂ F CH₂CH₃ CH₂CH₂CH₃ A-296 NO₂ F CH₂CH₃ CH₂CH₂OCH₃ A-297 NO₂ F CH₂OCH₃ CH₃ A-298 NO₂ F CH₂OCH₃ CH₂CH₃ A-299 NO₂ F CH₂OCH₃ CH₂CH₂CH₃ A-300 NO₂ F CH₂OCH₃ CH₂CH₂OCH₃ A-301 NO₂ F CH₂OCH₂CH₃ CH₃ A-302 NO₂ F CH₂OCH₂CH₃ CH₂CH₃ A-303 NO₂ F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-304 NO₂ F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-305 NO₂ F CH₂(CO)OCH₃ CH₃ A-306 NO₂ F CH₂(CO)OCH₃ CH₂CH₃ A-307 NO₂ F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-308 NO₂ F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-309 NO₂ F CH₂CHCH₂ CH₃ A-310 NO₂ F CH₂CHCH₂ CH₂CH₃ A-311 NO₂ F CH₂CHCH₂ CH₂CH₂CH₃ A-312 NO₂ F CH₂CHCH₂ CH₂CH₂OCH₃ A-313 NO₂ F CH₂CCH CH₃ A-314 NO₂ F CH₂CCH CH₂CH₃ A-315 NO₂ F CH₂CCH CH₂CH₂CH₃ A-316 NO₂ F CH₂CCH CH₂CH₂OCH₃ A-317 NO₂ F H CH₃ A-318 NO₂ F H CH₂CH₃ A-319 NO₂ F H CH₂CH₂CH₃ A-320 NO₂ F H CH₂CH₂OCH₃ A-321 NO₂ Cl CH₃ CH₃ A-322 NO₂ Cl CH₃ CH₂CH₃ A-323 NO₂ Cl CH₃ CH₂CH₂CH₃ A-324 NO₂ Cl CH₃ CH₂CH₂OCH₃ A-325 NO₂ Cl CH₂CH₃ CH₃ A-326 NO₂ Cl CH₂CH₃ CH₂CH₃ A-327 NO₂ Cl CH₂CH₃ CH₂CH₂CH₃ A-328 NO₂ Cl CH₂CH₃ CH₂CH₂OCH₃ A-329 NO₂ Cl CH₂OCH₃ CH₃ A-330 NO₂ Cl CH₂OCH₃ CH₂CH₃ A-331 NO₂ Cl CH₂OCH₃ CH₂CH₂CH₃ A-332 NO₂ Cl CH₂OCH₃ CH₂CH₂OCH₃ A-333 NO₂ Cl CH₂OCH₂CH₃ CH₃ A-334 NO₂ Cl CH₂OCH₂CH₃ CH₂CH₃ A-335 NO₂ Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-336 NO₂ Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-337 NO₂ Cl CH₂(CO)OCH₃ CH₃ A-338 NO₂ Cl CH₂(CO)OCH₃ CH₂CH₃ A-339 NO₂ Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-340 NO₂ Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-341 NO₂ Cl CH₂CHCH₂ CH₃ A-342 NO₂ Cl CH₂CHCH₂ CH₂CH₃ A-343 NO₂ Cl CH₂CHCH₂ CH₂CH₂CH₃ A-344 NO₂ Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-345 NO₂ Cl CH₂CCH CH₃ A-346 NO₂ Cl CH₂CCH CH₂CH₃ A-347 NO₂ Cl CH₂CCH CH₂CH₂CH₃ A-348 NO₂ Cl CH₂CCH CH₂CH₂OCH₃ A-349 NO₂ Cl H CH₃ A-350 NO₂ Cl H CH₂CH₃ A-351 NO₂ Cl H CH₂CH₂CH₃ A-352 NO₂ Cl H CH₂CH₂OCH₃ A-353 NO₂ Br CH₃ CH₃ A-354 NO₂ Br CH₃ CH₂CH₃ A-355 NO₂ Br CH₃ CH₂CH₂CH₃ A-356 NO₂ Br CH₃ CH₂CH₂OCH₃ A-357 NO₂ Br CH₂CH₃ CH₃ A-358 NO₂ Br CH₂CH₃ CH₂CH₃ A-359 NO₂ Br CH₂CH₃ CH₂CH₂CH₃ A-360 NO₂ Br CH₂CH₃ CH₂CH₂OCH₃ A-361 NO₂ Br CH₂OCH₃ CH₃ A-362 NO₂ Br CH₂OCH₃ CH₂CH₃ A-363 NO₂ Br CH₂OCH₃ CH₂CH₂CH₃ A-364 NO₂ Br CH₂OCH₃ CH₂CH₂OCH₃ A-365 NO₂ Br CH₂OCH₂CH₃ CH₃ A-366 NO₂ Br CH₂OCH₂CH₃ CH₂CH₃ A-367 NO₂ Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-368 NO₂ Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-369 NO₂ Br CH₂(CO)OCH₃ CH₃ A-370 NO₂ Br CH₂(CO)OCH₃ CH₂CH₃ A-371 NO₂ Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-372 NO₂ Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-373 NO₂ Br CH₂CHCH₂ CH₃ A-374 NO₂ Br CH₂CHCH₂ CH₂CH₃ A-375 NO₂ Br CH₂CHCH₂ CH₂CH₂CH₃ A-376 NO₂ Br CH₂CHCH₂ CH₂CH₂OCH₃ A-377 NO₂ Br CH₂CCH CH₃ A-378 NO₂ Br CH₂CCH CH₂CH₃ A-379 NO₂ Br CH₂CCH CH₂CH₂CH₃ A-380 NO₂ Br CH₂CCH CH₂CH₂OCH₃ A-381 NO₂ Br H CH₃ A-382 NO₂ Br H CH₂CH₃ A-383 NO₂ Br H CH₂CH₂CH₃ A-384 NO₂ Br H CH₂CH₂OCH₃ A-385 NO₂ CN CH₃ CH₃ A-386 NO₂ CN CH₃ CH₂CH₃ A-387 NO₂ CN CH₃ CH₂CH₂CH₃ A-388 NO₂ CN CH₃ CH₂CH₂OCH₃ A-389 NO₂ CN CH₂CH₃ CH₃ A-390 NO₂ CN CH₂CH₃ CH₂CH₃ A-391 NO₂ CN CH₂CH₃ CH₂CH₂CH₃ A-392 NO₂ CN CH₂CH₃ CH₂CH₂OCH₃ A-393 NO₂ CN CH₂OCH₃ CH₃ A-394 NO₂ CN CH₂OCH₃ CH₂CH₃ A-395 NO₂ CN CH₂OCH₃ CH₂CH₂CH₃ A-396 NO₂ CN CH₂OCH₃ CH₂CH₂OCH₃ A-397 NO₂ CN CH₂OCH₂CH₃ CH₃ A-398 NO₂ CN CH₂OCH₂CH₃ CH₂CH₃ A-399 NO₂ CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-400 NO₂ CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-401 NO₂ CN CH₂(CO)OCH₃ CH₃ A-402 NO₂ CN CH₂(CO)OCH₃ CH₂CH₃ A-403 NO₂ CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-404 NO₂ CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-405 NO₂ CN CH₂CHCH₂ CH₃ A-406 NO₂ CN CH₂CHCH₂ CH₂CH₃ A-407 NO₂ CN CH₂CHCH₂ CH₂CH₂CH₃ A-408 NO₂ CN CH₂CHCH₂ CH₂CH₂OCH₃ A-409 NO₂ CN CH₂CCH CH₃ A-410 NO₂ CN CH₂CCH CH₂CH₃ A-411 NO₂ CN CH₂CCH CH₂CH₂CH₃ A-412 NO₂ CN CH₂CCH CH₂CH₂OCH₃ A-413 NO₂ CN H CH₃ A-414 NO₂ CN H CH₂CH₃ A-415 NO₂ CN H CH₂CH₂CH₃ A-416 NO₂ CN H CH₂CH₂OCH₃ A-417 NO₂ CH₃ CH₃ CH₃ A-418 NO₂ CH₃ CH₃ CH₂CH₃ A-419 NO₂ CH₃ CH₃ CH₂CH₂CH₃ A-420 NO₂ CH₃ CH₃ CH₂CH₂OCH₃ A-421 NO₂ CH₃ CH₂CH₃ CH₃ A-422 NO₂ CH₃ CH₂CH₃ CH₂CH₃ A-423 NO₂ CH₃ CH₂CH₃ CH₂CH₂CH₃ A-424 NO₂ CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-425 NO₂ CH₃ CH₂OCH₃ CH₃ A-426 NO₂ CH₃ CH₂OCH₃ CH₂CH₃ A-427 NO₂ CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-428 NO₂ CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-429 NO₂ CH₃ CH₂OCH₂CH₃ CH₃ A-430 NO₂ CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-431 NO₂ CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-432 NO₂ CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-433 NO₂ CH₃ CH₂(CO)OCH₃ CH₃ A-434 NO₂ CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-435 NO₂ CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-436 NO₂ CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-437 NO₂ CH₃ CH₂CHCH₂ CH₃ A-438 NO₂ CH₃ CH₂CHCH₂ CH₂CH₃ A-439 NO₂ CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-440 NO₂ CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-441 NO₂ CH₃ CH₂CCH CH₃ A-442 NO₂ CH₃ CH₂CCH CH₂CH₃ A-443 NO₂ CH₃ CH₂CCH CH₂CH₂CH₃ A-444 NO₂ CH₃ CH₂CCH CH₂CH₂OCH₃ A-445 NO₂ CH₃ H CH₃ A-446 NO₂ CH₃ H CH₂CH₃ A-447 NO₂ CH₃ H CH₂CH₂CH₃ A-448 NO₂ CH₃ H CH₂CH₂OCH₃ A-449 NO₂ CF₃ CH₃ CH₃ A-450 NO₂ CF₃ CH₃ CH₂CH₃ A-451 NO₂ CF₃ CH₃ CH₂CH₂CH₃ A-452 NO₂ CF₃ CH₃ CH₂CH₂OCH₃ A-453 NO₂ CF₃ CH₂CH₃ CH₃ A-454 NO₂ CF₃ CH₂CH₃ CH₂CH₃ A-455 NO₂ CF₃ CH₂CH₃ CH₂CH₂CH₃ A-456 NO₂ CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-457 NO₂ CF₃ CH₂OCH₃ CH₃ A-458 NO₂ CF₃ CH₂OCH₃ CH₂CH₃ A-459 NO₂ CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-460 NO₂ CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-461 NO₂ CF₃ CH₂OCH₂CH₃ CH₃ A-462 NO₂ CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-463 NO₂ CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-464 NO₂ CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-465 NO₂ CF₃ CH₂(CO)OCH₃ CH₃ A-466 NO₂ CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-467 NO₂ CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-468 NO₂ CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-469 NO₂ CF₃ CH₂CHCH₂ CH₃ A-470 NO₂ CF₃ CH₂CHCH₂ CH₂CH₃ A-471 NO₂ CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-472 NO₂ CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-473 NO₂ CF₃ CH₂CCH CH₃ A-474 NO₂ CF₃ CH₂CCH CH₂CH₃ A-475 NO₂ CF₃ CH₂CCH CH₂CH₂CH₃ A-476 NO₂ CF₃ CH₂CCH CH₂CH₂OCH₃ A-477 NO₂ CF₃ H CH₃ A-478 NO₂ CF₃ H CH₂CH₃ A-479 NO₂ CF₃ H CH₂CH₂CH₃ A-480 NO₂ CF₃ H CH₂CH₂OCH₃ A-481 NO₂ SO₂CH₃ CH₃ CH₃ A-482 NO₂ SO₂CH₃ CH₃ CH₂CH₃ A-483 NO₂ SO₂CH₃ CH₃ CH₂CH₂CH₃ A-484 NO₂ SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-485 NO₂ SO₂CH₃ CH₂CH₃ CH₃ A-486 NO₂ SO₂CH₃ CH₂CH₃ CH₂CH₃ A-487 NO₂ SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-488 NO₂ SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-489 NO₂ SO₂CH₃ CH₂OCH₃ CH₃ A-490 NO₂ SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-491 NO₂ SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-492 NO₂ SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-493 NO₂ SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-494 NO₂ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-495 NO₂ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-496 NO₂ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-497 NO₂ SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-498 NO₂ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-499 NO₂ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-500 NO₂ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-501 NO₂ SO₂CH₃ CH₂CHCH₂ CH₃ A-502 NO₂ SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-503 NO₂ SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-504 NO₂ SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-505 NO₂ SO₂CH₃ CH₂CCH CH₃ A-506 NO₂ SO₂CH₃ CH₂CCH CH₂CH₃ A-507 NO₂ SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-508 NO₂ SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-509 NO₂ SO₂CH₃ H CH₃ A-510 NO₂ SO₂CH₃ H CH₂CH₃ A-511 NO₂ SO₂CH₃ H CH₂CH₂CH₃ A-512 NO₂ SO₂CH₃ H CH₂CH₂OCH₃ A-513 CH₃ H CH₃ CH₃ A-514 CH₃ H CH₃ CH₂CH₃ A-515 CH₃ H CH₃ CH₂CH₂CH₃ A-516 CH₃ H CH₃ CH₂CH₂OCH₃ A-517 CH₃ H CH₂CH₃ CH₃ A-518 CH₃ H CH₂CH₃ CH₂CH₃ A-519 CH₃ H CH₂CH₃ CH₂CH₂CH₃ A-520 CH₃ H CH₂CH₃ CH₂CH₂OCH₃ A-521 CH₃ H CH₂OCH₃ CH₃ A-522 CH₃ H CH₂OCH₃ CH₂CH₃ A-523 CH₃ H CH₂OCH₃ CH₂CH₂CH₃ A-524 CH₃ H CH₂OCH₃ CH₂CH₂OCH₃ A-525 CH₃ H CH₂OCH₂CH₃ CH₃ A-526 CH₃ H CH₂OCH₂CH₃ CH₂CH₃ A-527 CH₃ H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-528 CH₃ H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-529 CH₃ H CH₂(CO)OCH₃ CH₃ A-530 CH₃ H CH₂(CO)OCH₃ CH₂CH₃ A-531 CH₃ H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-532 CH₃ H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-533 CH₃ H CH₂CHCH₂ CH₃ A-534 CH₃ H CH₂CHCH₂ CH₂CH₃ A-535 CH₃ H CH₂CHCH₂ CH₂CH₂CH₃ A-536 CH₃ H CH₂CHCH₂ CH₂CH₂OCH₃ A-537 CH₃ H CH₂CCH CH₃ A-538 CH₃ H CH₂CCH CH₂CH₃ A-539 CH₃ H CH₂CCH CH₂CH₂CH₃ A-540 CH₃ H CH₂CCH CH₂CH₂OCH₃ A-541 CH₃ H H CH₃ A-542 CH₃ H H CH₂CH₃ A-543 CH₃ H H CH₂CH₂CH₃ A-544 CH₃ H H CH₂CH₂OCH₃ A-545 CH₃ F CH₃ CH₃ A-546 CH₃ F CH₃ CH₂CH₃ A-547 CH₃ F CH₃ CH₂CH₂CH₃ A-548 CH₃ F CH₃ CH₂CH₂OCH₃ A-549 CH₃ F CH₂CH₃ CH₃ A-550 CH₃ F CH₂CH₃ CH₂CH₃ A-551 CH₃ F CH₂CH₃ CH₂CH₂CH₃ A-552 CH₃ F CH₂CH₃ CH₂CH₂OCH₃ A-553 CH₃ F CH₂OCH₃ CH₃ A-554 CH₃ F CH₂OCH₃ CH₂CH₃ A-555 CH₃ F CH₂OCH₃ CH₂CH₂CH₃ A-556 CH₃ F CH₂OCH₃ CH₂CH₂OCH₃ A-557 CH₃ F CH₂OCH₂CH₃ CH₃ A-558 CH₃ F CH₂OCH₂CH₃ CH₂CH₃ A-559 CH₃ F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-560 CH₃ F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-561 CH₃ F CH₂(CO)OCH₃ CH₃ A-562 CH₃ F CH₂(CO)OCH₃ CH₂CH₃ A-563 CH₃ F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-564 CH₃ F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-565 CH₃ F CH₂CHCH₂ CH₃ A-566 CH₃ F CH₂CHCH₂ CH₂CH₃ A-567 CH₃ F CH₂CHCH₂ CH₂CH₂CH₃ A-568 CH₃ F CH₂CHCH₂ CH₂CH₂OCH₃ A-569 CH₃ F CH₂CCH CH₃ A-570 CH₃ F CH₂CCH CH₂CH₃ A-571 CH₃ F CH₂CCH CH₂CH₂CH₃ A-572 CH₃ F CH₂CCH CH₂CH₂OCH₃ A-573 CH₃ F H CH₃ A-574 CH₃ F H CH₂CH₃ A-575 CH₃ F H CH₂CH₂CH₃ A-576 CH₃ F H CH₂CH₂OCH₃ A-577 CH₃ Cl CH₃ CH₃ A-578 CH₃ Cl CH₃ CH₂CH₃ A-579 CH₃ Cl CH₃ CH₂CH₂CH₃ A-580 CH₃ Cl CH₃ CH₂CH₂OCH₃ A-581 CH₃ Cl CH₂CH₃ CH₃ A-582 CH₃ Cl CH₂CH₃ CH₂CH₃ A-583 CH₃ Cl CH₂CH₃ CH₂CH₂CH₃ A-584 CH₃ Cl CH₂CH₃ CH₂CH₂OCH₃ A-585 CH₃ Cl CH₂OCH₃ CH₃ A-586 CH₃ Cl CH₂OCH₃ CH₂CH₃ A-587 CH₃ Cl CH₂OCH₃ CH₂CH₂CH₃ A-588 CH₃ Cl CH₂OCH₃ CH₂CH₂OCH₃ A-589 CH₃ Cl CH₂OCH₂CH₃ CH₃ A-590 CH₃ Cl CH₂OCH₂CH₃ CH₂CH₃ A-591 CH₃ Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-592 CH₃ Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-593 CH₃ Cl CH₂(CO)OCH₃ CH₃ A-594 CH₃ Cl CH₂(CO)OCH₃ CH₂CH₃ A-595 CH₃ Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-596 CH₃ Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-597 CH₃ Cl CH₂CHCH₂ CH₃ A-598 CH₃ Cl CH₂CHCH₂ CH₂CH₃ A-599 CH₃ Cl CH₂CHCH₂ CH₂CH₂CH₃ A-600 CH₃ Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-601 CH₃ Cl CH₂CCH CH₃ A-602 CH₃ Cl CH₂CCH CH₂CH₃ A-603 CH₃ Cl CH₂CCH CH₂CH₂CH₃ A-604 CH₃ Cl CH₂CCH CH₂CH₂OCH₃ A-605 CH₃ Cl H CH₃ A-606 CH₃ Cl H CH₂CH₃ A-607 CH₃ Cl H CH₂CH₂CH₃ A-608 CH₃ Cl H CH₂CH₂OCH₃ A-609 CH₃ Br CH₃ CH₃ A-610 CH₃ Br CH₃ CH₂CH₃ A-611 CH₃ Br CH₃ CH₂CH₂CH₃ A-612 CH₃ Br CH₃ CH₂CH₂OCH₃ A-613 CH₃ Br CH₂CH₃ CH₃ A-614 CH₃ Br CH₂CH₃ CH₂CH₃ A-615 CH₃ Br CH₂CH₃ CH₂CH₂CH₃ A-616 CH₃ Br CH₂CH₃ CH₂CH₂OCH₃ A-617 CH₃ Br CH₂OCH₃ CH₃ A-618 CH₃ Br CH₂OCH₃ CH₂CH₃ A-619 CH₃ Br CH₂OCH₃ CH₂CH₂CH₃ A-620 CH₃ Br CH₂OCH₃ CH₂CH₂OCH₃ A-621 CH₃ Br CH₂OCH₂CH₃ CH₃ A-622 CH₃ Br CH₂OCH₂CH₃ CH₂CH₃ A-623 CH₃ Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-624 CH₃ Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-625 CH₃ Br CH₂(CO)OCH₃ CH₃ A-626 CH₃ Br CH₂(CO)OCH₃ CH₂CH₃ A-627 CH₃ Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-628 CH₃ Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-629 CH₃ Br CH₂CHCH₂ CH₃ A-630 CH₃ Br CH₂CHCH₂ CH₂CH₃ A-631 CH₃ Br CH₂CHCH₂ CH₂CH₂CH₃ A-632 CH₃ Br CH₂CHCH₂ CH₂CH₂OCH₃ A-633 CH₃ Br CH₂CCH CH₃ A-634 CH₃ Br CH₂CCH CH₂CH₃ A-635 CH₃ Br CH₂CCH CH₂CH₂CH₃ A-636 CH₃ Br CH₂CCH CH₂CH₂OCH₃ A-637 CH₃ Br H CH₃ A-638 CH₃ Br H CH₂CH₃ A-639 CH₃ Br H CH₂CH₂CH₃ A-640 CH₃ Br H CH₂CH₂OCH₃ A-641 CH₃ CN CH₃ CH₃ A-642 CH₃ CN CH₃ CH₂CH₃ A-643 CH₃ CN CH₃ CH₂CH₂CH₃ A-644 CH₃ CN CH₃ CH₂CH₂OCH₃ A-645 CH₃ CN CH₂CH₃ CH₃ A-646 CH₃ CN CH₂CH₃ CH₂CH₃ A-647 CH₃ CN CH₂CH₃ CH₂CH₂CH₃ A-648 CH₃ CN CH₂CH₃ CH₂CH₂OCH₃ A-649 CH₃ CN CH₂OCH₃ CH₃ A-650 CH₃ CN CH₂OCH₃ CH₂CH₃ A-651 CH₃ CN CH₂OCH₃ CH₂CH₂CH₃ A-652 CH₃ CN CH₂OCH₃ CH₂CH₂OCH₃ A-653 CH₃ CN CH₂OCH₂CH₃ CH₃ A-654 CH₃ CN CH₂OCH₂CH₃ CH₂CH₃ A-655 CH₃ CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-656 CH₃ CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-657 CH₃ CN CH₂(CO)OCH₃ CH₃ A-658 CH₃ CN CH₂(CO)OCH₃ CH₂CH₃ A-659 CH₃ CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-660 CH₃ CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-661 CH₃ CN CH₂CHCH₂ CH₃ A-662 CH₃ CN CH₂CHCH₂ CH₂CH₃ A-663 CH₃ CN CH₂CHCH₂ CH₂CH₂CH₃ A-664 CH₃ CN CH₂CHCH₂ CH₂CH₂OCH₃ A-665 CH₃ CN CH₂CCH CH₃ A-666 CH₃ CN CH₂CCH CH₂CH₃ A-667 CH₃ CN CH₂CCH CH₂CH₂CH₃ A-668 CH₃ CN CH₂CCH CH₂CH₂OCH₃ A-669 CH₃ CN H CH₃ A-670 CH₃ CN H CH₂CH₃ A-671 CH₃ CN H CH₂CH₂CH₃ A-672 CH₃ CN H CH₂CH₂OCH₃ A-673 CH₃ CH₃ CH₃ CH₃ A-674 CH₃ CH₃ CH₃ CH₂CH₃ A-675 CH₃ CH₃ CH₃ CH₂CH₂CH₃ A-676 CH₃ CH₃ CH₃ CH₂CH₂OCH₃ A-677 CH₃ CH₃ CH₂CH₃ CH₃ A-678 CH₃ CH₃ CH₂CH₃ CH₂CH₃ A-679 CH₃ CH₃ CH₂CH₃ CH₂CH₂CH₃ A-680 CH₃ CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-681 CH₃ CH₃ CH₂OCH₃ CH₃ A-682 CH₃ CH₃ CH₂OCH₃ CH₂CH₃ A-683 CH₃ CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-684 CH₃ CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-685 CH₃ CH₃ CH₂OCH₂CH₃ CH₃ A-686 CH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-687 CH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-688 CH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-689 CH₃ CH₃ CH₂(CO)OCH₃ CH₃ A-690 CH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-691 CH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-692 CH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-693 CH₃ CH₃ CH₂CHCH₂ CH₃ A-694 CH₃ CH₃ CH₂CHCH₂ CH₂CH₃ A-695 CH₃ CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-696 CH₃ CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-697 CH₃ CH₃ CH₂CCH CH₃ A-698 CH₃ CH₃ CH₂CCH CH₂CH₃ A-699 CH₃ CH₃ CH₂CCH CH₂CH₂CH₃ A-700 CH₃ CH₃ CH₂CCH CH₂CH₂OCH₃ A-701 CH₃ CH₃ H CH₃ A-702 CH₃ CH₃ H CH₂CH₃ A-703 CH₃ CH₃ H CH₂CH₂CH₃ A-704 CH₃ CH₃ H CH₂CH₂OCH₃ A-705 CH₃ CF₃ CH₃ CH₃ A-706 CH₃ CF₃ CH₃ CH₂CH₃ A-707 CH₃ CF₃ CH₃ CH₂CH₂CH₃ A-708 CH₃ CF₃ CH₃ CH₂CH₂OCH₃ A-709 CH₃ CF₃ CH₂CH₃ CH₃ A-710 CH₃ CF₃ CH₂CH₃ CH₂CH₃ A-711 CH₃ CF₃ CH₂CH₃ CH₂CH₂CH₃ A-712 CH₃ CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-713 CH₃ CF₃ CH₂OCH₃ CH₃ A-714 CH₃ CF₃ CH₂OCH₃ CH₂CH₃ A-715 CH₃ CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-716 CH₃ CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-717 CH₃ CF₃ CH₂OCH₂CH₃ CH₃ A-718 CH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-719 CH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-720 CH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-721 CH₃ CF₃ CH₂(CO)OCH₃ CH₃ A-722 CH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-723 CH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-724 CH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-725 CH₃ CF₃ CH₂CHCH₂ CH₃ A-726 CH₃ CF₃ CH₂CHCH₂ CH₂CH₃ A-727 CH₃ CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-728 CH₃ CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-729 CH₃ CF₃ CH₂CCH CH₃ A-730 CH₃ CF₃ CH₂CCH CH₂CH₃ A-731 CH₃ CF₃ CH₂CCH CH₂CH₂CH₃ A-732 CH₃ CF₃ CH₂CCH CH₂CH₂OCH₃ A-733 CH₃ CF₃ H CH₃ A-734 CH₃ CF₃ H CH₂CH₃ A-735 CH₃ CF₃ H CH₂CH₂CH₃ A-736 CH₃ CF₃ H CH₂CH₂OCH₃ A-737 CH₃ SO₂CH₃ CH₃ CH₃ A-738 CH₃ SO₂CH₃ CH₃ CH₂CH₃ A-739 CH₃ SO₂CH₃ CH₃ CH₂CH₂CH₃ A-740 CH₃ SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-741 CH₃ SO₂CH₃ CH₂CH₃ CH₃ A-742 CH₃ SO₂CH₃ CH₂CH₃ CH₂CH₃ A-743 CH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-744 CH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-745 CH₃ SO₂CH₃ CH₂OCH₃ CH₃ A-746 CH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-747 CH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-748 CH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-749 CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-750 CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-751 CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-752 CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-753 CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-754 CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-755 CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-756 CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-757 CH₃ SO₂CH₃ CH₂CHCH₂ CH₃ A-758 CH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-759 CH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-760 CH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-761 CH₃ SO₂CH₃ CH₂CCH CH₃ A-762 CH₃ SO₂CH₃ CH₂CCH CH₂CH₃ A-763 CH₃ SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-764 CH₃ SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-765 CH₃ SO₂CH₃ H CH₃ A-766 CH₃ SO₂CH₃ H CH₂CH₃ A-767 CH₃ SO₂CH₃ H CH₂CH₂CH₃ A-768 CH₃ SO₂CH₃ H CH₂CH₂OCH₃ A-769 cyclopropyl H CH₃ CH₃ A-770 cyclopropyl H CH₃ CH₂CH₃ A-771 cyclopropyl H CH₃ CH₂CH₂CH₃ A-772 cyclopropyl H CH₃ CH₂CH₂OCH₃ A-773 cyclopropyl H CH₂CH₃ CH₃ A-774 cyclopropyl H CH₂CH₃ CH₂CH₃ A-775 cyclopropyl H CH₂CH₃ CH₂CH₂CH₃ A-776 cyclopropyl H CH₂CH₃ CH₂CH₂OCH₃ A-777 cyclopropyl H CH₂OCH₃ CH₃ A-778 cyclopropyl H CH₂OCH₃ CH₂CH₃ A-779 cyclopropyl H CH₂OCH₃ CH₂CH₂CH₃ A-780 cyclopropyl H CH₂OCH₃ CH₂CH₂OCH₃ A-781 cyclopropyl H CH₂OCH₂CH₃ CH₃ A-782 cyclopropyl H CH₂OCH₂CH₃ CH₂CH₃ A-783 cyclopropyl H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-784 cyclopropyl H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-785 cyclopropyl H CH₂(CO)OCH₃ CH₃ A-786 cyclopropyl H CH₂(CO)OCH₃ CH₂CH₃ A-787 cyclopropyl H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-788 cyclopropyl H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-789 cyclopropyl H CH₂CHCH₂ CH₃ A-790 cyclopropyl H CH₂CHCH₂ CH₂CH₃ A-791 cyclopropyl H CH₂CHCH₂ CH₂CH₂CH₃ A-792 cyclopropyl H CH₂CHCH₂ CH₂CH₂OCH₃ A-793 cyclopropyl H CH₂CCH CH₃ A-794 cyclopropyl H CH₂CCH CH₂CH₃ A-795 cyclopropyl H CH₂CCH CH₂CH₂CH₃ A-796 cyclopropyl H CH₂CCH CH₂CH₂OCH₃ A-797 cyclopropyl H H CH₃ A-798 cyclopropyl H H CH₂CH₃ A-799 cyclopropyl H H CH₂CH₂CH₃ A-800 cyclopropyl H H CH₂CH₂OCH₃ A-801 cyclopropyl F CH₃ CH₃ A-802 cyclopropyl F CH₃ CH₂CH₃ A-803 cyclopropyl F CH₃ CH₂CH₂CH₃ A-804 cyclopropyl F CH₃ CH₂CH₂OCH₃ A-805 cyclopropyl F CH₂CH₃ CH₃ A-806 cyclopropyl F CH₂CH₃ CH₂CH₃ A-807 cyclopropyl F CH₂CH₃ CH₂CH₂CH₃ A-808 cyclopropyl F CH₂CH₃ CH₂CH₂OCH₃ A-809 cyclopropyl F CH₂OCH₃ CH₃ A-810 cyclopropyl F CH₂OCH₃ CH₂CH₃ A-811 cyclopropyl F CH₂OCH₃ CH₂CH₂CH₃ A-812 cyclopropyl F CH₂OCH₃ CH₂CH₂OCH₃ A-813 cyclopropyl F CH₂OCH₂CH₃ CH₃ A-814 cyclopropyl F CH₂OCH₂CH₃ CH₂CH₃ A-815 cyclopropyl F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-816 cyclopropyl F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-817 cyclopropyl F CH₂(CO)OCH₃ CH₃ A-818 cyclopropyl F CH₂(CO)OCH₃ CH₂CH₃ A-819 cyclopropyl F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-820 cyclopropyl F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-821 cyclopropyl F CH₂CHCH₂ CH₃ A-822 cyclopropyl F CH₂CHCH₂ CH₂CH₃ A-823 cyclopropyl F CH₂CHCH₂ CH₂CH₂CH₃ A-824 cyclopropyl F CH₂CHCH₂ CH₂CH₂OCH₃ A-825 cyclopropyl F CH₂CCH CH₃ A-826 cyclopropyl F CH₂CCH CH₂CH₃ A-827 cyclopropyl F CH₂CCH CH₂CH₂CH₃ A-828 cyclopropyl F CH₂CCH CH₂CH₂OCH₃ A-829 cyclopropyl F H CH₃ A-830 cyclopropyl F H CH₂CH₃ A-831 cyclopropyl F H CH₂CH₂CH₃ A-832 cyclopropyl F H CH₂CH₂OCH₃ A-833 cyclopropyl Cl CH₃ CH₃ A-834 cyclopropyl Cl CH₃ CH₂CH₃ A-835 cyclopropyl Cl CH₃ CH₂CH₂CH₃ A-836 cyclopropyl Cl CH₃ CH₂CH₂OCH₃ A-837 cyclopropyl Cl CH₂CH₃ CH₃ A-838 cyclopropyl Cl CH₂CH₃ CH₂CH₃ A-839 cyclopropyl Cl CH₂CH₃ CH₂CH₂CH₃ A-840 cyclopropyl Cl CH₂CH₃ CH₂CH₂OCH₃ A-841 cyclopropyl Cl CH₂OCH₃ CH₃ A-842 cyclopropyl Cl CH₂OCH₃ CH₂CH₃ A-843 cyclopropyl Cl CH₂OCH₃ CH₂CH₂CH₃ A-844 cyclopropyl Cl CH₂OCH₃ CH₂CH₂OCH₃ A-845 cyclopropyl Cl CH₂OCH₂CH₃ CH₃ A-846 cyclopropyl Cl CH₂OCH₂CH₃ CH₂CH₃ A-847 cyclopropyl Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-848 cyclopropyl Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-849 cyclopropyl Cl CH₂(CO)OCH₃ CH₃ A-850 cyclopropyl Cl CH₂(CO)OCH₃ CH₂CH₃ A-851 cyclopropyl Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-852 cyclopropyl Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-853 cyclopropyl Cl CH₂CHCH₂ CH₃ A-854 cyclopropyl Cl CH₂CHCH₂ CH₂CH₃ A-855 cyclopropyl Cl CH₂CHCH₂ CH₂CH₂CH₃ A-856 cyclopropyl Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-857 cyclopropyl Cl CH₂CCH CH₃ A-858 cyclopropyl Cl CH₂CCH CH₂CH₃ A-859 cyclopropyl Cl CH₂CCH CH₂CH₂CH₃ A-860 cyclopropyl Cl CH₂CCH CH₂CH₂OCH₃ A-861 cyclopropyl Cl H CH₃ A-862 cyclopropyl Cl H CH₂CH₃ A-863 cyclopropyl Cl H CH₂CH₂CH₃ A-864 cyclopropyl Cl H CH₂CH₂OCH₃ A-865 cyclopropyl Br CH₃ CH₃ A-866 cyclopropyl Br CH₃ CH₂CH₃ A-867 cyclopropyl Br CH₃ CH₂CH₂CH₃ A-868 cyclopropyl Br CH₃ CH₂CH₂OCH₃ A-869 cyclopropyl Br CH₂CH₃ CH₃ A-870 cyclopropyl Br CH₂CH₃ CH₂CH₃ A-871 cyclopropyl Br CH₂CH₃ CH₂CH₂CH₃ A-872 cyclopropyl Br CH₂CH₃ CH₂CH₂OCH₃ A-873 cyclopropyl Br CH₂OCH₃ CH₃ A-874 cyclopropyl Br CH₂OCH₃ CH₂CH₃ A-875 cyclopropyl Br CH₂OCH₃ CH₂CH₂CH₃ A-876 cyclopropyl Br CH₂OCH₃ CH₂CH₂OCH₃ A-877 cyclopropyl Br CH₂OCH₂CH₃ CH₃ A-878 cyclopropyl Br CH₂OCH₂CH₃ CH₂CH₃ A-879 cyclopropyl Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-880 cyclopropyl Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-881 cyclopropyl Br CH₂(CO)OCH₃ CH₃ A-882 cyclopropyl Br CH₂(CO)OCH₃ CH₂CH₃ A-883 cyclopropyl Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-884 cyclopropyl Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-885 cyclopropyl Br CH₂CHCH₂ CH₃ A-886 cyclopropyl Br CH₂CHCH₂ CH₂CH₃ A-887 cyclopropyl Br CH₂CHCH₂ CH₂CH₂CH₃ A-888 cyclopropyl Br CH₂CHCH₂ CH₂CH₂OCH₃ A-889 cyclopropyl Br CH₂CCH CH₃ A-890 cyclopropyl Br CH₂CCH CH₂CH₃ A-891 cyclopropyl Br CH₂CCH CH₂CH₂CH₃ A-892 cyclopropyl Br CH₂CCH CH₂CH₂OCH₃ A-893 cyclopropyl Br H CH₃ A-894 cyclopropyl Br H CH₂CH₃ A-895 cyclopropyl Br H CH₂CH₂CH₃ A-896 cyclopropyl Br H CH₂CH₂OCH₃ A-897 cyclopropyl CN CH₃ CH₃ A-898 cyclopropyl CN CH₃ CH₂CH₃ A-899 cyclopropyl CN CH₃ CH₂CH₂CH₃ A-900 cyclopropyl CN CH₃ CH₂CH₂OCH₃ A-901 cyclopropyl CN CH₂CH₃ CH₃ A-902 cyclopropyl CN CH₂CH₃ CH₂CH₃ A-903 cyclopropyl CN CH₂CH₃ CH₂CH₂CH₃ A-904 cyclopropyl CN CH₂CH₃ CH₂CH₂OCH₃ A-905 cyclopropyl CN CH₂OCH₃ CH₃ A-906 cyclopropyl CN CH₂OCH₃ CH₂CH₃ A-907 cyclopropyl CN CH₂OCH₃ CH₂CH₂CH₃ A-908 cyclopropyl CN CH₂OCH₃ CH₂CH₂OCH₃ A-909 cyclopropyl CN CH₂OCH₂CH₃ CH₃ A-910 cyclopropyl CN CH₂OCH₂CH₃ CH₂CH₃ A-911 cyclopropyl CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-912 cyclopropyl CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-913 cyclopropyl CN CH₂(CO)OCH₃ CH₃ A-914 cyclopropyl CN CH₂(CO)OCH₃ CH₂CH₃ A-915 cyclopropyl CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-916 cyclopropyl CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-917 cyclopropyl CN CH₂CHCH₂ CH₃ A-918 cyclopropyl CN CH₂CHCH₂ CH₂CH₃ A-919 cyclopropyl CN CH₂CHCH₂ CH₂CH₂CH₃ A-920 cyclopropyl CN CH₂CHCH₂ CH₂CH₂OCH₃ A-921 cyclopropyl CN CH₂CCH CH₃ A-922 cyclopropyl CN CH₂CCH CH₂CH₃ A-923 cyclopropyl CN CH₂CCH CH₂CH₂CH₃ A-924 cyclopropyl CN CH₂CCH CH₂CH₂OCH₃ A-925 cyclopropyl CN H CH₃ A-926 cyclopropyl CN H CH₂CH₃ A-927 cyclopropyl CN H CH₂CH₂CH₃ A-928 cyclopropyl CN H CH₂CH₂OCH₃ A-929 cyclopropyl CH₃ CH₃ CH₃ A-930 cyclopropyl CH₃ CH₃ CH₂CH₃ A-931 cyclopropyl CH₃ CH₃ CH₂CH₂CH₃ A-932 cyclopropyl CH₃ CH₃ CH₂CH₂OCH₃ A-933 cyclopropyl CH₃ CH₂CH₃ CH₃ A-934 cyclopropyl CH₃ CH₂CH₃ CH₂CH₃ A-935 cyclopropyl CH₃ CH₂CH₃ CH₂CH₂CH₃ A-936 cyclopropyl CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-937 cyclopropyl CH₃ CH₂OCH₃ CH₃ A-938 cyclopropyl CH₃ CH₂OCH₃ CH₂CH₃ A-939 cyclopropyl CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-940 cyclopropyl CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-941 cyclopropyl CH₃ CH₂OCH₂CH₃ CH₃ A-942 cyclopropyl CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-943 cyclopropyl CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-944 cyclopropyl CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-945 cyclopropyl CH₃ CH₂(CO)OCH₃ CH₃ A-946 cyclopropyl CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-947 cyclopropyl CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-948 cyclopropyl CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-949 cyclopropyl CH₃ CH₂CHCH₂ CH₃ A-950 cyclopropyl CH₃ CH₂CHCH₂ CH₂CH₃ A-951 cyclopropyl CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-952 cyclopropyl CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-953 cyclopropyl CH₃ CH₂CCH CH₃ A-954 cyclopropyl CH₃ CH₂CCH CH₂CH₃ A-955 cyclopropyl CH₃ CH₂CCH CH₂CH₂CH₃ A-956 cyclopropyl CH₃ CH₂CCH CH₂CH₂OCH₃ A-957 cyclopropyl CH₃ H CH₃ A-958 cyclopropyl CH₃ H CH₂CH₃ A-959 cyclopropyl CH₃ H CH₂CH₂CH₃ A-960 cyclopropyl CH₃ H CH₂CH₂OCH₃ A-961 cyclopropyl CF₃ CH₃ CH₃ A-962 cyclopropyl CF₃ CH₃ CH₂CH₃ A-963 cyclopropyl CF₃ CH₃ CH₂CH₂CH₃ A-964 cyclopropyl CF₃ CH₃ CH₂CH₂OCH₃ A-965 cyclopropyl CF₃ CH₂CH₃ CH₃ A-966 cyclopropyl CF₃ CH₂CH₃ CH₂CH₃ A-967 cyclopropyl CF₃ CH₂CH₃ CH₂CH₂CH₃ A-968 cyclopropyl CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-969 cyclopropyl CF₃ CH₂OCH₃ CH₃ A-970 cyclopropyl CF₃ CH₂OCH₃ CH₂CH₃ A-971 cyclopropyl CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-972 cyclopropyl CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-973 cyclopropyl CF₃ CH₂OCH₂CH₃ CH₃ A-974 cyclopropyl CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-975 cyclopropyl CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-976 cyclopropyl CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-977 cyclopropyl CF₃ CH₂(CO)OCH₃ CH₃ A-978 cyclopropyl CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-979 cyclopropyl CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-980 cyclopropyl CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-981 cyclopropyl CF₃ CH₂CHCH₂ CH₃ A-982 cyclopropyl CF₃ CH₂CHCH₂ CH₂CH₃ A-983 cyclopropyl CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-984 cyclopropyl CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-985 cyclopropyl CF₃ CH₂CCH CH₃ A-986 cyclopropyl CF₃ CH₂CCH CH₂CH₃ A-987 cyclopropyl CF₃ CH₂CCH CH₂CH₂CH₃ A-988 cyclopropyl CF₃ CH₂CCH CH₂CH₂OCH₃ A-989 cyclopropyl CF₃ H CH₃ A-990 cyclopropyl CF₃ H CH₂CH₃ A-991 cyclopropyl CF₃ H CH₂CH₂CH₃ A-992 cyclopropyl CF₃ H CH₂CH₂OCH₃ A-993 cyclopropyl SO₂CH₃ CH₃ CH₃ A-994 cyclopropyl SO₂CH₃ CH₃ CH₂CH₃ A-995 cyclopropyl SO₂CH₃ CH₃ CH₂CH₂CH₃ A-996 cyclopropyl SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-997 cyclopropyl SO₂CH₃ CH₂CH₃ CH₃ A-998 cyclopropyl SO₂CH₃ CH₂CH₃ CH₂CH₃ A-999 cyclopropyl SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1000 cyclopropyl SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1001 cyclopropyl SO₂CH₃ CH₂OCH₃ CH₃ A-1002 cyclopropyl SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-1003 cyclopropyl SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1004 cyclopropyl SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1005 cyclopropyl SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-1006 cyclopropyl SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1007 cyclopropyl SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1008 cyclopropyl SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1009 cyclopropyl SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-1010 cyclopropyl SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1011 cyclopropyl SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1012 cyclopropyl SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1013 cyclopropyl SO₂CH₃ CH₂CHCH₂ CH₃ A-1014 cyclopropyl SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-1015 cyclopropyl SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1016 cyclopropyl SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1017 cyclopropyl SO₂CH₃ CH₂CCH CH₃ A-1018 cyclopropyl SO₂CH₃ CH₂CCH CH₂CH₃ A-1019 cyclopropyl SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-1020 cyclopropyl SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-1021 cyclopropyl SO₂CH₃ H CH₃ A-1022 cyclopropyl SO₂CH₃ H CH₂CH₃ A-1023 cyclopropyl SO₂CH₃ H CH₂CH₂CH₃ A-1024 cyclopropyl SO₂CH₃ H CH₂CH₂OCH₃ A-1025 CH₂OCH₃ H CH₃ CH₃ A-1026 CH₂OCH₃ H CH₃ CH₂CH₃ A-1027 CH₂OCH₃ H CH₃ CH₂CH₂CH₃ A-1028 CH₂OCH₃ H CH₃ CH₂CH₂OCH₃ A-1029 CH₂OCH₃ H CH₂CH₃ CH₃ A-1030 CH₂OCH₃ H CH₂CH₃ CH₂CH₃ A-1031 CH₂OCH₃ H CH₂CH₃ CH₂CH₂CH₃ A-1032 CH₂OCH₃ H CH₂CH₃ CH₂CH₂OCH₃ A-1033 CH₂OCH₃ H CH₂OCH₃ CH₃ A-1034 CH₂OCH₃ H CH₂OCH₃ CH₂CH₃ A-1035 CH₂OCH₃ H CH₂OCH₃ CH₂CH₂CH₃ A-1036 CH₂OCH₃ H CH₂OCH₃ CH₂CH₂OCH₃ A-1037 CH₂OCH₃ H CH₂OCH₂CH₃ CH₃ A-1038 CH₂OCH₃ H CH₂OCH₂CH₃ CH₂CH₃ A-1039 CH₂OCH₃ H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1040 CH₂OCH₃ H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1041 CH₂OCH₃ H CH₂(CO)OCH₃ CH₃ A-1042 CH₂OCH₃ H CH₂(CO)OCH₃ CH₂CH₃ A-1043 CH₂OCH₃ H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1044 CH₂OCH₃ H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1045 CH₂OCH₃ H CH₂CHCH₂ CH₃ A-1046 CH₂OCH₃ H CH₂CHCH₂ CH₂CH₃ A-1047 CH₂OCH₃ H CH₂CHCH₂ CH₂CH₂CH₃ A-1048 CH₂OCH₃ H CH₂CHCH₂ CH₂CH₂OCH₃ A-1049 CH₂OCH₃ H CH₂CCH CH₃ A-1050 CH₂OCH₃ H CH₂CCH CH₂CH₃ A-1051 CH₂OCH₃ H CH₂CCH CH₂CH₂CH₃ A-1052 CH₂OCH₃ H CH₂CCH CH₂CH₂OCH₃ A-1053 CH₂OCH₃ H H CH₃ A-1054 CH₂OCH₃ H H CH₂CH₃ A-1055 CH₂OCH₃ H H CH₂CH₂CH₃ A-1056 CH₂OCH₃ H H CH₂CH₂OCH₃ A-1057 CH₂OCH₃ F CH₃ CH₃ A-1058 CH₂OCH₃ F CH₃ CH₂CH₃ A-1059 CH₂OCH₃ F CH₃ CH₂CH₂CH₃ A-1060 CH₂OCH₃ F CH₃ CH₂CH₂OCH₃ A-1061 CH₂OCH₃ F CH₂CH₃ CH₃ A-1062 CH₂OCH₃ F CH₂CH₃ CH₂CH₃ A-1063 CH₂OCH₃ F CH₂CH₃ CH₂CH₂CH₃ A-1064 CH₂OCH₃ F CH₂CH₃ CH₂CH₂OCH₃ A-1065 CH₂OCH₃ F CH₂OCH₃ CH₃ A-1066 CH₂OCH₃ F CH₂OCH₃ CH₂CH₃ A-1067 CH₂OCH₃ F CH₂OCH₃ CH₂CH₂CH₃ A-1068 CH₂OCH₃ F CH₂OCH₃ CH₂CH₂OCH₃ A-1069 CH₂OCH₃ F CH₂OCH₂CH₃ CH₃ A-1070 CH₂OCH₃ F CH₂OCH₂CH₃ CH₂CH₃ A-1071 CH₂OCH₃ F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1072 CH₂OCH₃ F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1073 CH₂OCH₃ F CH₂(CO)OCH₃ CH₃ A-1074 CH₂OCH₃ F CH₂(CO)OCH₃ CH₂CH₃ A-1075 CH₂OCH₃ F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1076 CH₂OCH₃ F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1077 CH₂OCH₃ F CH₂CHCH₂ CH₃ A-1078 CH₂OCH₃ F CH₂CHCH₂ CH₂CH₃ A-1079 CH₂OCH₃ F CH₂CHCH₂ CH₂CH₂CH₃ A-1080 CH₂OCH₃ F CH₂CHCH₂ CH₂CH₂OCH₃ A-1081 CH₂OCH₃ F CH₂CCH CH₃ A-1082 CH₂OCH₃ F CH₂CCH CH₂CH₃ A-1083 CH₂OCH₃ F CH₂CCH CH₂CH₂CH₃ A-1084 CH₂OCH₃ F CH₂CCH CH₂CH₂OCH₃ A-1085 CH₂OCH₃ F H CH₃ A-1086 CH₂OCH₃ F H CH₂CH₃ A-1087 CH₂OCH₃ F H CH₂CH₂CH₃ A-1088 CH₂OCH₃ F H CH₂CH₂OCH₃ A-1089 CH₂OCH₃ Cl CH₃ CH₃ A-1090 CH₂OCH₃ Cl CH₃ CH₂CH₃ A-1091 CH₂OCH₃ Cl CH₃ CH₂CH₂CH₃ A-1092 CH₂OCH₃ Cl CH₃ CH₂CH₂OCH₃ A-1093 CH₂OCH₃ Cl CH₂CH₃ CH₃ A-1094 CH₂OCH₃ Cl CH₂CH₃ CH₂CH₃ A-1095 CH₂OCH₃ Cl CH₂CH₃ CH₂CH₂CH₃ A-1096 CH₂OCH₃ Cl CH₂CH₃ CH₂CH₂OCH₃ A-1097 CH₂OCH₃ Cl CH₂OCH₃ CH₃ A-1098 CH₂OCH₃ Cl CH₂OCH₃ CH₂CH₃ A-1099 CH₂OCH₃ Cl CH₂OCH₃ CH₂CH₂CH₃ A-1100 CH₂OCH₃ Cl CH₂OCH₃ CH₂CH₂OCH₃ A-1101 CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₃ A-1102 CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₂CH₃ A-1103 CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1104 CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1105 CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₃ A-1106 CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₂CH₃ A-1107 CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1108 CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1109 CH₂OCH₃ Cl CH₂CHCH₂ CH₃ A-1110 CH₂OCH₃ Cl CH₂CHCH₂ CH₂CH₃ A-1111 CH₂OCH₃ Cl CH₂CHCH₂ CH₂CH₂CH₃ A-1112 CH₂OCH₃ Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-1113 CH₂OCH₃ Cl CH₂CCH CH₃ A-1114 CH₂OCH₃ Cl CH₂CCH CH₂CH₃ A-1115 CH₂OCH₃ Cl CH₂CCH CH₂CH₂CH₃ A-1116 CH₂OCH₃ Cl CH₂CCH CH₂CH₂OCH₃ A-1117 CH₂OCH₃ Cl H CH₃ A-1118 CH₂OCH₃ Cl H CH₂CH₃ A-1119 CH₂OCH₃ Cl H CH₂CH₂CH₃ A-1120 CH₂OCH₃ Cl H CH₂CH₂OCH₃ A-1121 CH₂OCH₃ Br CH₃ CH₃ A-1122 CH₂OCH₃ Br CH₃ CH₂CH₃ A-1123 CH₂OCH₃ Br CH₃ CH₂CH₂CH₃ A-1124 CH₂OCH₃ Br CH₃ CH₂CH₂OCH₃ A-1125 CH₂OCH₃ Br CH₂CH₃ CH₃ A-1126 CH₂OCH₃ Br CH₂CH₃ CH₂CH₃ A-1127 CH₂OCH₃ Br CH₂CH₃ CH₂CH₂CH₃ A-1128 CH₂OCH₃ Br CH₂CH₃ CH₂CH₂OCH₃ A-1129 CH₂OCH₃ Br CH₂OCH₃ CH₃ A-1130 CH₂OCH₃ Br CH₂OCH₃ CH₂CH₃ A-1131 CH₂OCH₃ Br CH₂OCH₃ CH₂CH₂CH₃ A-1132 CH₂OCH₃ Br CH₂OCH₃ CH₂CH₂OCH₃ A-1133 CH₂OCH₃ Br CH₂OCH₂CH₃ CH₃ A-1134 CH₂OCH₃ Br CH₂OCH₂CH₃ CH₂CH₃ A-1135 CH₂OCH₃ Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1136 CH₂OCH₃ Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1137 CH₂OCH₃ Br CH₂(CO)OCH₃ CH₃ A-1138 CH₂OCH₃ Br CH₂(CO)OCH₃ CH₂CH₃ A-1139 CH₂OCH₃ Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1140 CH₂OCH₃ Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1141 CH₂OCH₃ Br CH₂CHCH₂ CH₃ A-1142 CH₂OCH₃ Br CH₂CHCH₂ CH₂CH₃ A-1143 CH₂OCH₃ Br CH₂CHCH₂ CH₂CH₂CH₃ A-1144 CH₂OCH₃ Br CH₂CHCH₂ CH₂CH₂OCH₃ A-1145 CH₂OCH₃ Br CH₂CCH CH₃ A-1146 CH₂OCH₃ Br CH₂CCH CH₂CH₃ A-1147 CH₂OCH₃ Br CH₂CCH CH₂CH₂CH₃ A-1148 CH₂OCH₃ Br CH₂CCH CH₂CH₂OCH₃ A-1149 CH₂OCH₃ Br H CH₃ A-1150 CH₂OCH₃ Br H CH₂CH₃ A-1151 CH₂OCH₃ Br H CH₂CH₂CH₃ A-1152 CH₂OCH₃ Br H CH₂CH₂OCH₃ A-1153 CH₂OCH₃ CN CH₃ CH₃ A-1154 CH₂OCH₃ CN CH₃ CH₂CH₃ A-1155 CH₂OCH₃ CN CH₃ CH₂CH₂CH₃ A-1156 CH₂OCH₃ CN CH₃ CH₂CH₂OCH₃ A-1157 CH₂OCH₃ CN CH₂CH₃ CH₃ A-1158 CH₂OCH₃ CN CH₂CH₃ CH₂CH₃ A-1159 CH₂OCH₃ CN CH₂CH₃ CH₂CH₂CH₃ A-1160 CH₂OCH₃ CN CH₂CH₃ CH₂CH₂OCH₃ A-1161 CH₂OCH₃ CN CH₂OCH₃ CH₃ A-1162 CH₂OCH₃ CN CH₂OCH₃ CH₂CH₃ A-1163 CH₂OCH₃ CN CH₂OCH₃ CH₂CH₂CH₃ A-1164 CH₂OCH₃ CN CH₂OCH₃ CH₂CH₂OCH₃ A-1165 CH₂OCH₃ CN CH₂OCH₂CH₃ CH₃ A-1166 CH₂OCH₃ CN CH₂OCH₂CH₃ CH₂CH₃ A-1167 CH₂OCH₃ CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1168 CH₂OCH₃ CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1169 CH₂OCH₃ CN CH₂(CO)OCH₃ CH₃ A-1170 CH₂OCH₃ CN CH₂(CO)OCH₃ CH₂CH₃ A-1171 CH₂OCH₃ CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1172 CH₂OCH₃ CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1173 CH₂OCH₃ CN CH₂CHCH₂ CH₃ A-1174 CH₂OCH₃ CN CH₂CHCH₂ CH₂CH₃ A-1175 CH₂OCH₃ CN CH₂CHCH₂ CH₂CH₂CH₃ A-1176 CH₂OCH₃ CN CH₂CHCH₂ CH₂CH₂OCH₃ A-1177 CH₂OCH₃ CN CH₂CCH CH₃ A-1178 CH₂OCH₃ CN CH₂CCH CH₂CH₃ A-1179 CH₂OCH₃ CN CH₂CCH CH₂CH₂CH₃ A-1180 CH₂OCH₃ CN CH₂CCH CH₂CH₂OCH₃ A-1181 CH₂OCH₃ CN H CH₃ A-1182 CH₂OCH₃ CN H CH₂CH₃ A-1183 CH₂OCH₃ CN H CH₂CH₂CH₃ A-1184 CH₂OCH₃ CN H CH₂CH₂OCH₃ A-1185 CH₂OCH₃ CH₃ CH₃ CH₃ A-1186 CH₂OCH₃ CH₃ CH₃ CH₂CH₃ A-1187 CH₂OCH₃ CH₃ CH₃ CH₂CH₂CH₃ A-1188 CH₂OCH₃ CH₃ CH₃ CH₂CH₂OCH₃ A-1189 CH₂OCH₃ CH₃ CH₂CH₃ CH₃ A-1190 CH₂OCH₃ CH₃ CH₂CH₃ CH₂CH₃ A-1191 CH₂OCH₃ CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1192 CH₂OCH₃ CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1193 CH₂OCH₃ CH₃ CH₂OCH₃ CH₃ A-1194 CH₂OCH₃ CH₃ CH₂OCH₃ CH₂CH₃ A-1195 CH₂OCH₃ CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1196 CH₂OCH₃ CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1197 CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₃ A-1198 CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1199 CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1200 CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1201 CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₃ A-1202 CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1203 CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1204 CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1205 CH₂OCH₃ CH₃ CH₂CHCH₂ CH₃ A-1206 CH₂OCH₃ CH₃ CH₂CHCH₂ CH₂CH₃ A-1207 CH₂OCH₃ CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1208 CH₂OCH₃ CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1209 CH₂OCH₃ CH₃ CH₂CCH CH₃ A-1210 CH₂OCH₃ CH₃ CH₂CCH CH₂CH₃ A-1211 CH₂OCH₃ CH₃ CH₂CCH CH₂CH₂CH₃ A-1212 CH₂OCH₃ CH₃ CH₂CCH CH₂CH₂OCH₃ A-1213 CH₂OCH₃ CH₃ H CH₃ A-1214 CH₂OCH₃ CH₃ H CH₂CH₃ A-1215 CH₂OCH₃ CH₃ H CH₂CH₂CH₃ A-1216 CH₂OCH₃ CH₃ H CH₂CH₂OCH₃ A-1217 CH₂OCH₃ CF₃ CH₃ CH₃ A-1218 CH₂OCH₃ CF₃ CH₃ CH₂CH₃ A-1219 CH₂OCH₃ CF₃ CH₃ CH₂CH₂CH₃ A-1220 CH₂OCH₃ CF₃ CH₃ CH₂CH₂OCH₃ A-1221 CH₂OCH₃ CF₃ CH₂CH₃ CH₃ A-1222 CH₂OCH₃ CF₃ CH₂CH₃ CH₂CH₃ A-1223 CH₂OCH₃ CF₃ CH₂CH₃ CH₂CH₂CH₃ A-1224 CH₂OCH₃ CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-1225 CH₂OCH₃ CF₃ CH₂OCH₃ CH₃ A-1226 CH₂OCH₃ CF₃ CH₂OCH₃ CH₂CH₃ A-1227 CH₂OCH₃ CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-1228 CH₂OCH₃ CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1229 CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₃ A-1230 CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-1231 CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1232 CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1233 CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₃ A-1234 CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-1235 CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1236 CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1237 CH₂OCH₃ CF₃ CH₂CHCH₂ CH₃ A-1238 CH₂OCH₃ CF₃ CH₂CHCH₂ CH₂CH₃ A-1239 CH₂OCH₃ CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1240 CH₂OCH₃ CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1241 CH₂OCH₃ CF₃ CH₂CCH CH₃ A-1242 CH₂OCH₃ CF₃ CH₂CCH CH₂CH₃ A-1243 CH₂OCH₃ CF₃ CH₂CCH CH₂CH₂CH₃ A-1244 CH₂OCH₃ CF₃ CH₂CCH CH₂CH₂OCH₃ A-1245 CH₂OCH₃ CF₃ H CH₃ A-1246 CH₂OCH₃ CF₃ H CH₂CH₃ A-1247 CH₂OCH₃ CF₃ H CH₂CH₂CH₃ A-1248 CH₂OCH₃ CF₃ H CH₂CH₂OCH₃ A-1249 CH₂OCH₃ SO₂CH₃ CH₃ CH₃ A-1250 CH₂OCH₃ SO₂CH₃ CH₃ CH₂CH₃ A-1251 CH₂OCH₃ SO₂CH₃ CH₃ CH₂CH₂CH₃ A-1252 CH₂OCH₃ SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-1253 CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₃ A-1254 CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₂CH₃ A-1255 CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1256 CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1257 CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₃ A-1258 CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-1259 CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1260 CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1261 CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-1262 CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1263 CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1264 CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1265 CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-1266 CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1267 CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1268 CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1269 CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₃ A-1270 CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-1271 CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1272 CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1273 CH₂OCH₃ SO₂CH₃ CH₂CCH CH₃ A-1274 CH₂OCH₃ SO₂CH₃ CH₂CCH CH₂CH₃ A-1275 CH₂OCH₃ SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-1276 CH₂OCH₃ SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-1277 CH₂OCH₃ SO₂CH₃ H CH₃ A-1278 CH₂OCH₃ SO₂CH₃ H CH₂CH₃ A-1279 CH₂OCH₃ SO₂CH₃ H CH₂CH₂CH₃ A-1280 CH₂OCH₃ SO₂CH₃ H CH₂CH₂OCH₃ A-1281 CH₂OCH₂CH₂OCH₃ H CH₃ CH₃ A-1282 CH₂OCH₂CH₂OCH₃ H CH₃ CH₂CH₃ A-1283 CH₂OCH₂CH₂OCH₃ H CH₃ CH₂CH₂CH₃ A-1284 CH₂OCH₂CH₂OCH₃ H CH₃ CH₂CH₂OCH₃ A-1285 CH₂OCH₂CH₂OCH₃ H CH₂CH₃ CH₃ A-1286 CH₂OCH₂CH₂OCH₃ H CH₂CH₃ CH₂CH₃ A-1287 CH₂OCH₂CH₂OCH₃ H CH₂CH₃ CH₂CH₂CH₃ A-1288 CH₂OCH₂CH₂OCH₃ H CH₂CH₃ CH₂CH₂OCH₃ A-1289 CH₂OCH₂CH₂OCH₃ H CH₂OCH₃ CH₃ A-1290 CH₂OCH₂CH₂OCH₃ H CH₂OCH₃ CH₂CH₃ A-1291 CH₂OCH₂CH₂OCH₃ H CH₂OCH₃ CH₂CH₂CH₃ A-1292 CH₂OCH₂CH₂OCH₃ H CH₂OCH₃ CH₂CH₂OCH₃ A-1293 CH₂OCH₂CH₂OCH₃ H CH₂OCH₂CH₃ CH₃ A-1294 CH₂OCH₂CH₂OCH₃ H CH₂OCH₂CH₃ CH₂CH₃ A-1295 CH₂OCH₂CH₂OCH₃ H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1296 CH₂OCH₂CH₂OCH₃ H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1297 CH₂OCH₂CH₂OCH₃ H CH₂(CO)OCH₃ CH₃ A-1298 CH₂OCH₂CH₂OCH₃ H CH₂(CO)OCH₃ CH₂CH₃ A-1299 CH₂OCH₂CH₂OCH₃ H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1300 CH₂OCH₂CH₂OCH₃ H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1301 CH₂OCH₂CH₂OCH₃ H CH₂CHCH₂ CH₃ A-1302 CH₂OCH₂CH₂OCH₃ H CH₂CHCH₂ CH₂CH₃ A-1303 CH₂OCH₂CH₂OCH₃ H CH₂CHCH₂ CH₂CH₂CH₃ A-1304 CH₂OCH₂CH₂OCH₃ H CH₂CHCH₂ CH₂CH₂OCH₃ A-1305 CH₂OCH₂CH₂OCH₃ H CH₂CCH CH₃ A-1306 CH₂OCH₂CH₂OCH₃ H CH₂CCH CH₂CH₃ A-1307 CH₂OCH₂CH₂OCH₃ H CH₂CCH CH₂CH₂CH₃ A-1308 CH₂OCH₂CH₂OCH₃ H CH₂CCH CH₂CH₂OCH₃ A-1309 CH₂OCH₂CH₂OCH₃ H H CH₃ A-1310 CH₂OCH₂CH₂OCH₃ H H CH₂CH₃ A-1311 CH₂OCH₂CH₂OCH₃ H H CH₂CH₂CH₃ A-1312 CH₂OCH₂CH₂OCH₃ H H CH₂CH₂OCH₃ A-1313 CH₂OCH₂CH₂OCH₃ F CH₃ CH₃ A-1314 CH₂OCH₂CH₂OCH₃ F CH₃ CH₂CH₃ A-1315 CH₂OCH₂CH₂OCH₃ F CH₃ CH₂CH₂CH₃ A-1316 CH₂OCH₂CH₂OCH₃ F CH₃ CH₂CH₂OCH₃ A-1317 CH₂OCH₂CH₂OCH₃ F CH₂CH₃ CH₃ A-1318 CH₂OCH₂CH₂OCH₃ F CH₂CH₃ CH₂CH₃ A-1319 CH₂OCH₂CH₂OCH₃ F CH₂CH₃ CH₂CH₂CH₃ A-1320 CH₂OCH₂CH₂OCH₃ F CH₂CH₃ CH₂CH₂OCH₃ A-1321 CH₂OCH₂CH₂OCH₃ F CH₂OCH₃ CH₃ A-1322 CH₂OCH₂CH₂OCH₃ F CH₂OCH₃ CH₂CH₃ A-1323 CH₂OCH₂CH₂OCH₃ F CH₂OCH₃ CH₂CH₂CH₃ A-1324 CH₂OCH₂CH₂OCH₃ F CH₂OCH₃ CH₂CH₂OCH₃ A-1325 CH₂OCH₂CH₂OCH₃ F CH₂OCH₂CH₃ CH₃ A-1326 CH₂OCH₂CH₂OCH₃ F CH₂OCH₂CH₃ CH₂CH₃ A-1327 CH₂OCH₂CH₂OCH₃ F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1328 CH₂OCH₂CH₂OCH₃ F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1329 CH₂OCH₂CH₂OCH₃ F CH₂(CO)OCH₃ CH₃ A-1330 CH₂OCH₂CH₂OCH₃ F CH₂(CO)OCH₃ CH₂CH₃ A-1331 CH₂OCH₂CH₂OCH₃ F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1332 CH₂OCH₂CH₂OCH₃ F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1333 CH₂OCH₂CH₂OCH₃ F CH₂CHCH₂ CH₃ A-1334 CH₂OCH₂CH₂OCH₃ F CH₂CHCH₂ CH₂CH₃ A-1335 CH₂OCH₂CH₂OCH₃ F CH₂CHCH₂ CH₂CH₂CH₃ A-1336 CH₂OCH₂CH₂OCH₃ F CH₂CHCH₂ CH₂CH₂OCH₃ A-1337 CH₂OCH₂CH₂OCH₃ F CH₂CCH CH₃ A-1338 CH₂OCH₂CH₂OCH₃ F CH₂CCH CH₂CH₃ A-1339 CH₂OCH₂CH₂OCH₃ F CH₂CCH CH₂CH₂CH₃ A-1340 CH₂OCH₂CH₂OCH₃ F CH₂CCH CH₂CH₂OCH₃ A-1341 CH₂OCH₂CH₂OCH₃ F H CH₃ A-1342 CH₂OCH₂CH₂OCH₃ F H CH₂CH₃ A-1343 CH₂OCH₂CH₂OCH₃ F H CH₂CH₂CH₃ A-1344 CH₂OCH₂CH₂OCH₃ F H CH₂CH₂OCH₃ A-1345 CH₂OCH₂CH₂OCH₃ Cl CH₃ CH₃ A-1346 CH₂OCH₂CH₂OCH₃ Cl CH₃ CH₂CH₃ A-1347 CH₂OCH₂CH₂OCH₃ Cl CH₃ CH₂CH₂CH₃ A-1348 CH₂OCH₂CH₂OCH₃ Cl CH₃ CH₂CH₂OCH₃ A-1349 CH₂OCH₂CH₂OCH₃ Cl CH₂CH₃ CH₃ A-1350 CH₂OCH₂CH₂OCH₃ Cl CH₂CH₃ CH₂CH₃ A-1351 CH₂OCH₂CH₂OCH₃ Cl CH₂CH₃ CH₂CH₂CH₃ A-1352 CH₂OCH₂CH₂OCH₃ Cl CH₂CH₃ CH₂CH₂OCH₃ A-1353 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₃ CH₃ A-1354 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₃ CH₂CH₃ A-1355 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₃ CH₂CH₂CH₃ A-1356 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₃ CH₂CH₂OCH₃ A-1357 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₃ A-1358 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₂CH₃ A-1359 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1360 CH₂OCH₂CH₂OCH₃ Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1361 CH₂OCH₂CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₃ A-1362 CH₂OCH₂CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₂CH₃ A-1363 CH₂OCH₂CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1364 CH₂OCH₂CH₂OCH₃ Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1365 CH₂OCH₂CH₂OCH₃ Cl CH₂CHCH₂ CH₃ A-1366 CH₂OCH₂CH₂OCH₃ Cl CH₂CHCH₂ CH₂CH₃ A-1367 CH₂OCH₂CH₂OCH₃ Cl CH₂CHCH₂ CH₂CH₂CH₃ A-1368 CH₂OCH₂CH₂OCH₃ Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-1369 CH₂OCH₂CH₂OCH₃ Cl CH₂CCH CH₃ A-1370 CH₂OCH₂CH₂OCH₃ Cl CH₂CCH CH₂CH₃ A-1371 CH₂OCH₂CH₂OCH₃ Cl CH₂CCH CH₂CH₂CH₃ A-1372 CH₂OCH₂CH₂OCH₃ Cl CH₂CCH CH₂CH₂OCH₃ A-1373 CH₂OCH₂CH₂OCH₃ Cl H CH₃ A-1374 CH₂OCH₂CH₂OCH₃ Cl H CH₂CH₃ A-1375 CH₂OCH₂CH₂OCH₃ Cl H CH₂CH₂CH₃ A-1376 CH₂OCH₂CH₂OCH₃ Cl H CH₂CH₂OCH₃ A-1377 CH₂OCH₂CH₂OCH₃ Br CH₃ CH₃ A-1378 CH₂OCH₂CH₂OCH₃ Br CH₃ CH₂CH₃ A-1379 CH₂OCH₂CH₂OCH₃ Br CH₃ CH₂CH₂CH₃ A-1380 CH₂OCH₂CH₂OCH₃ Br CH₃ CH₂CH₂OCH₃ A-1381 CH₂OCH₂CH₂OCH₃ Br CH₂CH₃ CH₃ A-1382 CH₂OCH₂CH₂OCH₃ Br CH₂CH₃ CH₂CH₃ A-1383 CH₂OCH₂CH₂OCH₃ Br CH₂CH₃ CH₂CH₂CH₃ A-1384 CH₂OCH₂CH₂OCH₃ Br CH₂CH₃ CH₂CH₂OCH₃ A-1385 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₃ CH₃ A-1386 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₃ CH₂CH₃ A-1387 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₃ CH₂CH₂CH₃ A-1388 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₃ CH₂CH₂OCH₃ A-1389 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₂CH₃ CH₃ A-1390 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₂CH₃ CH₂CH₃ A-1391 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1392 CH₂OCH₂CH₂OCH₃ Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1393 CH₂OCH₂CH₂OCH₃ Br CH₂(CO)OCH₃ CH₃ A-1394 CH₂OCH₂CH₂OCH₃ Br CH₂(CO)OCH₃ CH₂CH₃ A-1395 CH₂OCH₂CH₂OCH₃ Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1396 CH₂OCH₂CH₂OCH₃ Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1397 CH₂OCH₂CH₂OCH₃ Br CH₂CHCH₂ CH₃ A-1398 CH₂OCH₂CH₂OCH₃ Br CH₂CHCH₂ CH₂CH₃ A-1399 CH₂OCH₂CH₂OCH₃ Br CH₂CHCH₂ CH₂CH₂CH₃ A-1400 CH₂OCH₂CH₂OCH₃ Br CH₂CHCH₂ CH₂CH₂OCH₃ A-1401 CH₂OCH₂CH₂OCH₃ Br CH₂CCH CH₃ A-1402 CH₂OCH₂CH₂OCH₃ Br CH₂CCH CH₂CH₃ A-1403 CH₂OCH₂CH₂OCH₃ Br CH₂CCH CH₂CH₂CH₃ A-1404 CH₂OCH₂CH₂OCH₃ Br CH₂CCH CH₂CH₂OCH₃ A-1405 CH₂OCH₂CH₂OCH₃ Br H CH₃ A-1406 CH₂OCH₂CH₂OCH₃ Br H CH₂CH₃ A-1407 CH₂OCH₂CH₂OCH₃ Br H CH₂CH₂CH₃ A-1408 CH₂OCH₂CH₂OCH₃ Br H CH₂CH₂OCH₃ A-1409 CH₂OCH₂CH₂OCH₃ CN CH₃ CH₃ A-1410 CH₂OCH₂CH₂OCH₃ CN CH₃ CH₂CH₃ A-1411 CH₂OCH₂CH₂OCH₃ CN CH₃ CH₂CH₂CH₃ A-1412 CH₂OCH₂CH₂OCH₃ CN CH₃ CH₂CH₂OCH₃ A-1413 CH₂OCH₂CH₂OCH₃ CN CH₂CH₃ CH₃ A-1414 CH₂OCH₂CH₂OCH₃ CN CH₂CH₃ CH₂CH₃ A-1415 CH₂OCH₂CH₂OCH₃ CN CH₂CH₃ CH₂CH₂CH₃ A-1416 CH₂OCH₂CH₂OCH₃ CN CH₂CH₃ CH₂CH₂OCH₃ A-1417 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₃ CH₃ A-1418 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₃ CH₂CH₃ A-1419 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₃ CH₂CH₂CH₃ A-1420 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₃ CH₂CH₂OCH₃ A-1421 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₂CH₃ CH₃ A-1422 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₂CH₃ CH₂CH₃ A-1423 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1424 CH₂OCH₂CH₂OCH₃ CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1425 CH₂OCH₂CH₂OCH₃ CN CH₂(CO)OCH₃ CH₃ A-1426 CH₂OCH₂CH₂OCH₃ CN CH₂(CO)OCH₃ CH₂CH₃ A-1427 CH₂OCH₂CH₂OCH₃ CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1428 CH₂OCH₂CH₂OCH₃ CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1429 CH₂OCH₂CH₂OCH₃ CN CH₂CHCH₂ CH₃ A-1430 CH₂OCH₂CH₂OCH₃ CN CH₂CHCH₂ CH₂CH₃ A-1431 CH₂OCH₂CH₂OCH₃ CN CH₂CHCH₂ CH₂CH₂CH₃ A-1432 CH₂OCH₂CH₂OCH₃ CN CH₂CHCH₂ CH₂CH₂OCH₃ A-1433 CH₂OCH₂CH₂OCH₃ CN CH₂CCH CH₃ A-1434 CH₂OCH₂CH₂OCH₃ CN CH₂CCH CH₂CH₃ A-1435 CH₂OCH₂CH₂OCH₃ CN CH₂CCH CH₂CH₂CH₃ A-1436 CH₂OCH₂CH₂OCH₃ CN CH₂CCH CH₂CH₂OCH₃ A-1437 CH₂OCH₂CH₂OCH₃ CN H CH₃ A-1438 CH₂OCH₂CH₂OCH₃ CN H CH₂CH₃ A-1439 CH₂OCH₂CH₂OCH₃ CN H CH₂CH₂CH₃ A-1440 CH₂OCH₂CH₂OCH₃ CN H CH₂CH₂OCH₃ A-1441 CH₂OCH₂CH₂OCH₃ CH₃ CH₃ CH₃ A-1442 CH₂OCH₂CH₂OCH₃ CH₃ CH₃ CH₂CH₃ A-1443 CH₂OCH₂CH₂OCH₃ CH₃ CH₃ CH₂CH₂CH₃ A-1444 CH₂OCH₂CH₂OCH₃ CH₃ CH₃ CH₂CH₂OCH₃ A-1445 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CH₃ CH₃ A-1446 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CH₃ CH₂CH₃ A-1447 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1448 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1449 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₃ CH₃ A-1450 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₃ CH₂CH₃ A-1451 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1452 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1453 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₃ A-1454 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1455 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1456 CH₂OCH₂CH₂OCH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1457 CH₂OCH₂CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₃ A-1458 CH₂OCH₂CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1459 CH₂OCH₂CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1460 CH₂OCH₂CH₂OCH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1461 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CHCH₂ CH₃ A-1462 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CHCH₂ CH₂CH₃ A-1463 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1464 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1465 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CCH CH₃ A-1466 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CCH CH₂CH₃ A-1467 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CCH CH₂CH₂CH₃ A-1468 CH₂OCH₂CH₂OCH₃ CH₃ CH₂CCH CH₂CH₂OCH₃ A-1469 CH₂OCH₂CH₂OCH₃ CH₃ H CH₃ A-1470 CH₂OCH₂CH₂OCH₃ CH₃ H CH₂CH₃ A-1471 CH₂OCH₂CH₂OCH₃ CH₃ H CH₂CH₂CH₃ A-1472 CH₂OCH₂CH₂OCH₃ CH₃ H CH₂CH₂OCH₃ A-1473 CH₂OCH₂CH₂OCH₃ CF₃ CH₃ CH₃ A-1474 CH₂OCH₂CH₂OCH₃ CF₃ CH₃ CH₂CH₃ A-1475 CH₂OCH₂CH₂OCH₃ CF₃ CH₃ CH₂CH₂CH₃ A-1476 CH₂OCH₂CH₂OCH₃ CF₃ CH₃ CH₂CH₂OCH₃ A-1477 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CH₃ CH₃ A-1478 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CH₃ CH₂CH₃ A-1479 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CH₃ CH₂CH₂CH₃ A-1480 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-1481 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₃ CH₃ A-1482 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₃ CH₂CH₃ A-1483 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-1484 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1485 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₃ A-1486 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-1487 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1488 CH₂OCH₂CH₂OCH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1489 CH₂OCH₂CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₃ A-1490 CH₂OCH₂CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-1491 CH₂OCH₂CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1492 CH₂OCH₂CH₂OCH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1493 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CHCH₂ CH₃ A-1494 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CHCH₂ CH₂CH₃ A-1495 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1496 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1497 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CCH CH₃ A-1498 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CCH CH₂CH₃ A-1499 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CCH CH₂CH₂CH₃ A-1500 CH₂OCH₂CH₂OCH₃ CF₃ CH₂CCH CH₂CH₂OCH₃ A-1501 CH₂OCH₂CH₂OCH₃ CF₃ H CH₃ A-1502 CH₂OCH₂CH₂OCH₃ CF₃ H CH₂CH₃ A-1503 CH₂OCH₂CH₂OCH₃ CF₃ H CH₂CH₂CH₃ A-1504 CH₂OCH₂CH₂OCH₃ CF₃ H CH₂CH₂OCH₃ A-1505 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₃ CH₃ A-1506 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₃ CH₂CH₃ A-1507 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₃ CH₂CH₂CH₃ A-1508 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-1509 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₃ A-1510 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₂CH₃ A-1511 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1512 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1513 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₃ A-1514 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-1515 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1516 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1517 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-1518 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1519 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1520 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1521 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-1522 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1523 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1524 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1525 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₃ A-1526 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-1527 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1528 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1529 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CCH CH₃ A-1530 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CCH CH₂CH₃ A-1531 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-1532 CH₂OCH₂CH₂OCH₃ SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-1533 CH₂OCH₂CH₂OCH₃ SO₂CH₃ H CH₃ A-1534 CH₂OCH₂CH₂OCH₃ SO₂CH₃ H CH₂CH₃ A-1535 CH₂OCH₂CH₂OCH₃ SO₂CH₃ H CH₂CH₂CH₃ A-1536 CH₂OCH₂CH₂OCH₃ SO₂CH₃ H CH₂CH₂OCH₃ A-1537 SO₂CH₃ H CH₃ CH₃ A-1538 SO₂CH₃ H CH₃ CH₂CH₃ A-1539 SO₂CH₃ H CH₃ CH₂CH₂CH₃ A-1540 SO₂CH₃ H CH₃ CH₂CH₂OCH₃ A-1541 SO₂CH₃ H CH₂CH₃ CH₃ A-1542 SO₂CH₃ H CH₂CH₃ CH₂CH₃ A-1543 SO₂CH₃ H CH₂CH₃ CH₂CH₂CH₃ A-1544 SO₂CH₃ H CH₂CH₃ CH₂CH₂OCH₃ A-1545 SO₂CH₃ H CH₂OCH₃ CH₃ A-1546 SO₂CH₃ H CH₂OCH₃ CH₂CH₃ A-1547 SO₂CH₃ H CH₂OCH₃ CH₂CH₂CH₃ A-1548 SO₂CH₃ H CH₂OCH₃ CH₂CH₂OCH₃ A-1549 SO₂CH₃ H CH₂OCH₂CH₃ CH₃ A-1550 SO₂CH₃ H CH₂OCH₂CH₃ CH₂CH₃ A-1551 SO₂CH₃ H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1552 SO₂CH₃ H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1553 SO₂CH₃ H CH₂(CO)OCH₃ CH₃ A-1554 SO₂CH₃ H CH₂(CO)OCH₃ CH₂CH₃ A-1555 SO₂CH₃ H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1556 SO₂CH₃ H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1557 SO₂CH₃ H CH₂CHCH₂ CH₃ A-1558 SO₂CH₃ H CH₂CHCH₂ CH₂CH₃ A-1559 SO₂CH₃ H CH₂CHCH₂ CH₂CH₂CH₃ A-1560 SO₂CH₃ H CH₂CHCH₂ CH₂CH₂OCH₃ A-1561 SO₂CH₃ H CH₂CCH CH₃ A-1562 SO₂CH₃ H CH₂CCH CH₂CH₃ A-1563 SO₂CH₃ H CH₂CCH CH₂CH₂CH₃ A-1564 SO₂CH₃ H CH₂CCH CH₂CH₂OCH₃ A-1565 SO₂CH₃ H H CH₃ A-1566 SO₂CH₃ H H CH₂CH₃ A-1567 SO₂CH₃ H H CH₂CH₂CH₃ A-1568 SO₂CH₃ H H CH₂CH₂OCH₃ A-1569 SO₂CH₃ F CH₃ CH₃ A-1570 SO₂CH₃ F CH₃ CH₂CH₃ A-1571 SO₂CH₃ F CH₃ CH₂CH₂CH₃ A-1572 SO₂CH₃ F CH₃ CH₂CH₂OCH₃ A-1573 SO₂CH₃ F CH₂CH₃ CH₃ A-1574 SO₂CH₃ F CH₂CH₃ CH₂CH₃ A-1575 SO₂CH₃ F CH₂CH₃ CH₂CH₂CH₃ A-1576 SO₂CH₃ F CH₂CH₃ CH₂CH₂OCH₃ A-1577 SO₂CH₃ F CH₂OCH₃ CH₃ A-1578 SO₂CH₃ F CH₂OCH₃ CH₂CH₃ A-1579 SO₂CH₃ F CH₂OCH₃ CH₂CH₂CH₃ A-1580 SO₂CH₃ F CH₂OCH₃ CH₂CH₂OCH₃ A-1581 SO₂CH₃ F CH₂OCH₂CH₃ CH₃ A-1582 SO₂CH₃ F CH₂OCH₂CH₃ CH₂CH₃ A-1583 SO₂CH₃ F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1584 SO₂CH₃ F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1585 SO₂CH₃ F CH₂(CO)OCH₃ CH₃ A-1586 SO₂CH₃ F CH₂(CO)OCH₃ CH₂CH₃ A-1587 SO₂CH₃ F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1588 SO₂CH₃ F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1589 SO₂CH₃ F CH₂CHCH₂ CH₃ A-1590 SO₂CH₃ F CH₂CHCH₂ CH₂CH₃ A-1591 SO₂CH₃ F CH₂CHCH₂ CH₂CH₂CH₃ A-1592 SO₂CH₃ F CH₂CHCH₂ CH₂CH₂OCH₃ A-1593 SO₂CH₃ F CH₂CCH CH₃ A-1594 SO₂CH₃ F CH₂CCH CH₂CH₃ A-1595 SO₂CH₃ F CH₂CCH CH₂CH₂CH₃ A-1596 SO₂CH₃ F CH₂CCH CH₂CH₂OCH₃ A-1597 SO₂CH₃ F H CH₃ A-1598 SO₂CH₃ F H CH₂CH₃ A-1599 SO₂CH₃ F H CH₂CH₂CH₃ A-1600 SO₂CH₃ F H CH₂CH₂OCH₃ A-1601 SO₂CH₃ Cl CH₃ CH₃ A-1602 SO₂CH₃ Cl CH₃ CH₂CH₃ A-1603 SO₂CH₃ Cl CH₃ CH₂CH₂CH₃ A-1604 SO₂CH₃ Cl CH₃ CH₂CH₂OCH₃ A-1605 SO₂CH₃ Cl CH₂CH₃ CH₃ A-1606 SO₂CH₃ Cl CH₂CH₃ CH₂CH₃ A-1607 SO₂CH₃ Cl CH₂CH₃ CH₂CH₂CH₃ A-1608 SO₂CH₃ Cl CH₂CH₃ CH₂CH₂OCH₃ A-1609 SO₂CH₃ Cl CH₂OCH₃ CH₃ A-1610 SO₂CH₃ Cl CH₂OCH₃ CH₂CH₃ A-1611 SO₂CH₃ Cl CH₂OCH₃ CH₂CH₂CH₃ A-1612 SO₂CH₃ Cl CH₂OCH₃ CH₂CH₂OCH₃ A-1613 SO₂CH₃ Cl CH₂OCH₂CH₃ CH₃ A-1614 SO₂CH₃ Cl CH₂OCH₂CH₃ CH₂CH₃ A-1615 SO₂CH₃ Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1616 SO₂CH₃ Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1617 SO₂CH₃ Cl CH₂(CO)OCH₃ CH₃ A-1618 SO₂CH₃ Cl CH₂(CO)OCH₃ CH₂CH₃ A-1619 SO₂CH₃ Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1620 SO₂CH₃ Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1621 SO₂CH₃ Cl CH₂CHCH₂ CH₃ A-1622 SO₂CH₃ Cl CH₂CHCH₂ CH₂CH₃ A-1623 SO₂CH₃ Cl CH₂CHCH₂ CH₂CH₂CH₃ A-1624 SO₂CH₃ Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-1625 SO₂CH₃ Cl CH₂CCH CH₃ A-1626 SO₂CH₃ Cl CH₂CCH CH₂CH₃ A-1627 SO₂CH₃ Cl CH₂CCH CH₂CH₂CH₃ A-1628 SO₂CH₃ Cl CH₂CCH CH₂CH₂OCH₃ A-1629 SO₂CH₃ Cl H CH₃ A-1630 SO₂CH₃ Cl H CH₂CH₃ A-1631 SO₂CH₃ Cl H CH₂CH₂CH₃ A-1632 SO₂CH₃ Cl H CH₂CH₂OCH₃ A-1633 SO₂CH₃ Br CH₃ CH₃ A-1634 SO₂CH₃ Br CH₃ CH₂CH₃ A-1635 SO₂CH₃ Br CH₃ CH₂CH₂CH₃ A-1636 SO₂CH₃ Br CH₃ CH₂CH₂OCH₃ A-1637 SO₂CH₃ Br CH₂CH₃ CH₃ A-1638 SO₂CH₃ Br CH₂CH₃ CH₂CH₃ A-1639 SO₂CH₃ Br CH₂CH₃ CH₂CH₂CH₃ A-1640 SO₂CH₃ Br CH₂CH₃ CH₂CH₂OCH₃ A-1641 SO₂CH₃ Br CH₂OCH₃ CH₃ A-1642 SO₂CH₃ Br CH₂OCH₃ CH₂CH₃ A-1643 SO₂CH₃ Br CH₂OCH₃ CH₂CH₂CH₃ A-1644 SO₂CH₃ Br CH₂OCH₃ CH₂CH₂OCH₃ A-1645 SO₂CH₃ Br CH₂OCH₂CH₃ CH₃ A-1646 SO₂CH₃ Br CH₂OCH₂CH₃ CH₂CH₃ A-1647 SO₂CH₃ Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1648 SO₂CH₃ Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1649 SO₂CH₃ Br CH₂(CO)OCH₃ CH₃ A-1650 SO₂CH₃ Br CH₂(CO)OCH₃ CH₂CH₃ A-1651 SO₂CH₃ Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1652 SO₂CH₃ Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1653 SO₂CH₃ Br CH₂CHCH₂ CH₃ A-1654 SO₂CH₃ Br CH₂CHCH₂ CH₂CH₃ A-1655 SO₂CH₃ Br CH₂CHCH₂ CH₂CH₂CH₃ A-1656 SO₂CH₃ Br CH₂CHCH₂ CH₂CH₂OCH₃ A-1657 SO₂CH₃ Br CH₂CCH CH₃ A-1658 SO₂CH₃ Br CH₂CCH CH₂CH₃ A-1659 SO₂CH₃ Br CH₂CCH CH₂CH₂CH₃ A-1660 SO₂CH₃ Br CH₂CCH CH₂CH₂OCH₃ A-1661 SO₂CH₃ Br H CH₃ A-1662 SO₂CH₃ Br H CH₂CH₃ A-1663 SO₂CH₃ Br H CH₂CH₂CH₃ A-1664 SO₂CH₃ Br H CH₂CH₂OCH₃ A-1665 SO₂CH₃ CN CH₃ CH₃ A-1666 SO₂CH₃ CN CH₃ CH₂CH₃ A-1667 SO₂CH₃ CN CH₃ CH₂CH₂CH₃ A-1668 SO₂CH₃ CN CH₃ CH₂CH₂OCH₃ A-1669 SO₂CH₃ CN CH₂CH₃ CH₃ A-1670 SO₂CH₃ CN CH₂CH₃ CH₂CH₃ A-1671 SO₂CH₃ CN CH₂CH₃ CH₂CH₂CH₃ A-1672 SO₂CH₃ CN CH₂CH₃ CH₂CH₂OCH₃ A-1673 SO₂CH₃ CN CH₂OCH₃ CH₃ A-1674 SO₂CH₃ CN CH₂OCH₃ CH₂CH₃ A-1675 SO₂CH₃ CN CH₂OCH₃ CH₂CH₂CH₃ A-1676 SO₂CH₃ CN CH₂OCH₃ CH₂CH₂OCH₃ A-1677 SO₂CH₃ CN CH₂OCH₂CH₃ CH₃ A-1678 SO₂CH₃ CN CH₂OCH₂CH₃ CH₂CH₃ A-1679 SO₂CH₃ CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1680 SO₂CH₃ CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1681 SO₂CH₃ CN CH₂(CO)OCH₃ CH₃ A-1682 SO₂CH₃ CN CH₂(CO)OCH₃ CH₂CH₃ A-1683 SO₂CH₃ CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1684 SO₂CH₃ CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1685 SO₂CH₃ CN CH₂CHCH₂ CH₃ A-1686 SO₂CH₃ CN CH₂CHCH₂ CH₂CH₃ A-1687 SO₂CH₃ CN CH₂CHCH₂ CH₂CH₂CH₃ A-1688 SO₂CH₃ CN CH₂CHCH₂ CH₂CH₂OCH₃ A-1689 SO₂CH₃ CN CH₂CCH CH₃ A-1690 SO₂CH₃ CN CH₂CCH CH₂CH₃ A-1691 SO₂CH₃ CN CH₂CCH CH₂CH₂CH₃ A-1692 SO₂CH₃ CN CH₂CCH CH₂CH₂OCH₃ A-1693 SO₂CH₃ CN H CH₃ A-1694 SO₂CH₃ CN H CH₂CH₃ A-1695 SO₂CH₃ CN H CH₂CH₂CH₃ A-1696 SO₂CH₃ CN H CH₂CH₂OCH₃ A-1697 SO₂CH₃ CH₃ CH₃ CH₃ A-1698 SO₂CH₃ CH₃ CH₃ CH₂CH₃ A-1699 SO₂CH₃ CH₃ CH₃ CH₂CH₂CH₃ A-1700 SO₂CH₃ CH₃ CH₃ CH₂CH₂OCH₃ A-1701 SO₂CH₃ CH₃ CH₂CH₃ CH₃ A-1702 SO₂CH₃ CH₃ CH₂CH₃ CH₂CH₃ A-1703 SO₂CH₃ CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1704 SO₂CH₃ CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1705 SO₂CH₃ CH₃ CH₂OCH₃ CH₃ A-1706 SO₂CH₃ CH₃ CH₂OCH₃ CH₂CH₃ A-1707 SO₂CH₃ CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1708 SO₂CH₃ CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1709 SO₂CH₃ CH₃ CH₂OCH₂CH₃ CH₃ A-1710 SO₂CH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1711 SO₂CH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1712 SO₂CH₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1713 SO₂CH₃ CH₃ CH₂(CO)OCH₃ CH₃ A-1714 SO₂CH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1715 SO₂CH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1716 SO₂CH₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1717 SO₂CH₃ CH₃ CH₂CHCH₂ CH₃ A-1718 SO₂CH₃ CH₃ CH₂CHCH₂ CH₂CH₃ A-1719 SO₂CH₃ CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1720 SO₂CH₃ CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1721 SO₂CH₃ CH₃ CH₂CCH CH₃ A-1722 SO₂CH₃ CH₃ CH₂CCH CH₂CH₃ A-1723 SO₂CH₃ CH₃ CH₂CCH CH₂CH₂CH₃ A-1724 SO₂CH₃ CH₃ CH₂CCH CH₂CH₂OCH₃ A-1725 SO₂CH₃ CH₃ H CH₃ A-1726 SO₂CH₃ CH₃ H CH₂CH₃ A-1727 SO₂CH₃ CH₃ H CH₂CH₂CH₃ A-1728 SO₂CH₃ CH₃ H CH₂CH₂OCH₃ A-1729 SO₂CH₃ CF₃ CH₃ CH₃ A-1730 SO₂CH₃ CF₃ CH₃ CH₂CH₃ A-1731 SO₂CH₃ CF₃ CH₃ CH₂CH₂CH₃ A-1732 SO₂CH₃ CF₃ CH₃ CH₂CH₂OCH₃ A-1733 SO₂CH₃ CF₃ CH₂CH₃ CH₃ A-1734 SO₂CH₃ CF₃ CH₂CH₃ CH₂CH₃ A-1735 SO₂CH₃ CF₃ CH₂CH₃ CH₂CH₂CH₃ A-1736 SO₂CH₃ CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-1737 SO₂CH₃ CF₃ CH₂OCH₃ CH₃ A-1738 SO₂CH₃ CF₃ CH₂OCH₃ CH₂CH₃ A-1739 SO₂CH₃ CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-1740 SO₂CH₃ CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1741 SO₂CH₃ CF₃ CH₂OCH₂CH₃ CH₃ A-1742 SO₂CH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-1743 SO₂CH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1744 SO₂CH₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1745 SO₂CH₃ CF₃ CH₂(CO)OCH₃ CH₃ A-1746 SO₂CH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-1747 SO₂CH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1748 SO₂CH₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1749 SO₂CH₃ CF₃ CH₂CHCH₂ CH₃ A-1750 SO₂CH₃ CF₃ CH₂CHCH₂ CH₂CH₃ A-1751 SO₂CH₃ CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1752 SO₂CH₃ CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1753 SO₂CH₃ CF₃ CH₂CCH CH₃ A-1754 SO₂CH₃ CF₃ CH₂CCH CH₂CH₃ A-1755 SO₂CH₃ CF₃ CH₂CCH CH₂CH₂CH₃ A-1756 SO₂CH₃ CF₃ CH₂CCH CH₂CH₂OCH₃ A-1757 SO₂CH₃ CF₃ H CH₃ A-1758 SO₂CH₃ CF₃ H CH₂CH₃ A-1759 SO₂CH₃ CF₃ H CH₂CH₂CH₃ A-1760 SO₂CH₃ CF₃ H CH₂CH₂OCH₃ A-1761 SO₂CH₃ SO₂CH₃ CH₃ CH₃ A-1762 SO₂CH₃ SO₂CH₃ CH₃ CH₂CH₃ A-1763 SO₂CH₃ SO₂CH₃ CH₃ CH₂CH₂CH₃ A-1764 SO₂CH₃ SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-1765 SO₂CH₃ SO₂CH₃ CH₂CH₃ CH₃ A-1766 SO₂CH₃ SO₂CH₃ CH₂CH₃ CH₂CH₃ A-1767 SO₂CH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1768 SO₂CH₃ SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1769 SO₂CH₃ SO₂CH₃ CH₂OCH₃ CH₃ A-1770 SO₂CH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-1771 SO₂CH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1772 SO₂CH₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1773 SO₂CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-1774 SO₂CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1775 SO₂CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1776 SO₂CH₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1777 SO₂CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-1778 SO₂CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1779 SO₂CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1780 SO₂CH₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1781 SO₂CH₃ SO₂CH₃ CH₂CHCH₂ CH₃ A-1782 SO₂CH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-1783 SO₂CH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1784 SO₂CH₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1785 SO₂CH₃ SO₂CH₃ CH₂CCH CH₃ A-1786 SO₂CH₃ SO₂CH₃ CH₂CCH CH₂CH₃ A-1787 SO₂CH₃ SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-1788 SO₂CH₃ SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-1789 SO₂CH₃ SO₂CH₃ H CH₃ A-1790 SO₂CH₃ SO₂CH₃ H CH₂CH₃ A-1791 SO₂CH₃ SO₂CH₃ H CH₂CH₂CH₃ A-1792 SO₂CH₃ SO₂CH₃ H CH₂CH₂OCH₃ A-1793 CF₃ H CH₃ CH₃ A-1794 CF₃ H CH₃ CH₂CH₃ A-1795 CF₃ H CH₃ CH₂CH₂CH₃ A-1796 CF₃ H CH₃ CH₂CH₂OCH₃ A-1797 CF₃ H CH₂CH₃ CH₃ A-1798 CF₃ H CH₂CH₃ CH₂CH₃ A-1799 CF₃ H CH₂CH₃ CH₂CH₂CH₃ A-1800 CF₃ H CH₂CH₃ CH₂CH₂OCH₃ A-1801 CF₃ H CH₂OCH₃ CH₃ A-1802 CF₃ H CH₂OCH₃ CH₂CH₃ A-1803 CF₃ H CH₂OCH₃ CH₂CH₂CH₃ A-1804 CF₃ H CH₂OCH₃ CH₂CH₂OCH₃ A-1805 CF₃ H CH₂OCH₂CH₃ CH₃ A-1806 CF₃ H CH₂OCH₂CH₃ CH₂CH₃ A-1807 CF₃ H CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1808 CF₃ H CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1809 CF₃ H CH₂(CO)OCH₃ CH₃ A-1810 CF₃ H CH₂(CO)OCH₃ CH₂CH₃ A-1811 CF₃ H CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1812 CF₃ H CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1813 CF₃ H CH₂CHCH₂ CH₃ A-1814 CF₃ H CH₂CHCH₂ CH₂CH₃ A-1815 CF₃ H CH₂CHCH₂ CH₂CH₂CH₃ A-1816 CF₃ H CH₂CHCH₂ CH₂CH₂OCH₃ A-1817 CF₃ H CH₂CCH CH₃ A-1818 CF₃ H CH₂CCH CH₂CH₃ A-1819 CF₃ H CH₂CCH CH₂CH₂CH₃ A-1820 CF₃ H CH₂CCH CH₂CH₂OCH₃ A-1821 CF₃ H H CH₃ A-1822 CF₃ H H CH₂CH₃ A-1823 CF₃ H H CH₂CH₂CH₃ A-1824 CF₃ H H CH₂CH₂OCH₃ A-1825 CF₃ F CH₃ CH₃ A-1826 CF₃ F CH₃ CH₂CH₃ A-1827 CF₃ F CH₃ CH₂CH₂CH₃ A-1828 CF₃ F CH₃ CH₂CH₂OCH₃ A-1829 CF₃ F CH₂CH₃ CH₃ A-1830 CF₃ F CH₂CH₃ CH₂CH₃ A-1831 CF₃ F CH₂CH₃ CH₂CH₂CH₃ A-1832 CF₃ F CH₂CH₃ CH₂CH₂OCH₃ A-1833 CF₃ F CH₂OCH₃ CH₃ A-1834 CF₃ F CH₂OCH₃ CH₂CH₃ A-1835 CF₃ F CH₂OCH₃ CH₂CH₂CH₃ A-1836 CF₃ F CH₂OCH₃ CH₂CH₂OCH₃ A-1837 CF₃ F CH₂OCH₂CH₃ CH₃ A-1838 CF₃ F CH₂OCH₂CH₃ CH₂CH₃ A-1839 CF₃ F CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1840 CF₃ F CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1841 CF₃ F CH₂(CO)OCH₃ CH₃ A-1842 CF₃ F CH₂(CO)OCH₃ CH₂CH₃ A-1843 CF₃ F CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1844 CF₃ F CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1845 CF₃ F CH₂CHCH₂ CH₃ A-1846 CF₃ F CH₂CHCH₂ CH₂CH₃ A-1847 CF₃ F CH₂CHCH₂ CH₂CH₂CH₃ A-1848 CF₃ F CH₂CHCH₂ CH₂CH₂OCH₃ A-1849 CF₃ F CH₂CCH CH₃ A-1850 CF₃ F CH₂CCH CH₂CH₃ A-1851 CF₃ F CH₂CCH CH₂CH₂CH₃ A-1852 CF₃ F CH₂CCH CH₂CH₂OCH₃ A-1853 CF₃ F H CH₃ A-1854 CF₃ F H CH₂CH₃ A-1855 CF₃ F H CH₂CH₂CH₃ A-1856 CF₃ F H CH₂CH₂OCH₃ A-1857 CF₃ Cl CH₃ CH₃ A-1858 CF₃ Cl CH₃ CH₂CH₃ A-1859 CF₃ Cl CH₃ CH₂CH₂CH₃ A-1860 CF₃ Cl CH₃ CH₂CH₂OCH₃ A-1861 CF₃ Cl CH₂CH₃ CH₃ A-1862 CF₃ Cl CH₂CH₃ CH₂CH₃ A-1863 CF₃ Cl CH₂CH₃ CH₂CH₂CH₃ A-1864 CF₃ Cl CH₂CH₃ CH₂CH₂OCH₃ A-1865 CF₃ Cl CH₂OCH₃ CH₃ A-1866 CF₃ Cl CH₂OCH₃ CH₂CH₃ A-1867 CF₃ Cl CH₂OCH₃ CH₂CH₂CH₃ A-1868 CF₃ Cl CH₂OCH₃ CH₂CH₂OCH₃ A-1869 CF₃ Cl CH₂OCH₂CH₃ CH₃ A-1870 CF₃ Cl CH₂OCH₂CH₃ CH₂CH₃ A-1871 CF₃ Cl CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1872 CF₃ Cl CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1873 CF₃ Cl CH₂(CO)OCH₃ CH₃ A-1874 CF₃ Cl CH₂(CO)OCH₃ CH₂CH₃ A-1875 CF₃ Cl CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1876 CF₃ Cl CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1877 CF₃ Cl CH₂CHCH₂ CH₃ A-1878 CF₃ Cl CH₂CHCH₂ CH₂CH₃ A-1879 CF₃ Cl CH₂CHCH₂ CH₂CH₂CH₃ A-1880 CF₃ Cl CH₂CHCH₂ CH₂CH₂OCH₃ A-1881 CF₃ Cl CH₂CCH CH₃ A-1882 CF₃ Cl CH₂CCH CH₂CH₃ A-1883 CF₃ Cl CH₂CCH CH₂CH₂CH₃ A-1884 CF₃ Cl CH₂CCH CH₂CH₂OCH₃ A-1885 CF₃ Cl H CH₃ A-1886 CF₃ Cl H CH₂CH₃ A-1887 CF₃ Cl H CH₂CH₂CH₃ A-1888 CF₃ Cl H CH₂CH₂OCH₃ A-1889 CF₃ Br CH₃ CH₃ A-1890 CF₃ Br CH₃ CH₂CH₃ A-1891 CF₃ Br CH₃ CH₂CH₂CH₃ A-1892 CF₃ Br CH₃ CH₂CH₂OCH₃ A-1893 CF₃ Br CH₂CH₃ CH₃ A-1894 CF₃ Br CH₂CH₃ CH₂CH₃ A-1895 CF₃ Br CH₂CH₃ CH₂CH₂CH₃ A-1896 CF₃ Br CH₂CH₃ CH₂CH₂OCH₃ A-1897 CF₃ Br CH₂OCH₃ CH₃ A-1898 CF₃ Br CH₂OCH₃ CH₂CH₃ A-1899 CF₃ Br CH₂OCH₃ CH₂CH₂CH₃ A-1900 CF₃ Br CH₂OCH₃ CH₂CH₂OCH₃ A-1901 CF₃ Br CH₂OCH₂CH₃ CH₃ A-1902 CF₃ Br CH₂OCH₂CH₃ CH₂CH₃ A-1903 CF₃ Br CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1904 CF₃ Br CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1905 CF₃ Br CH₂(CO)OCH₃ CH₃ A-1906 CF₃ Br CH₂(CO)OCH₃ CH₂CH₃ A-1907 CF₃ Br CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1908 CF₃ Br CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1909 CF₃ Br CH₂CHCH₂ CH₃ A-1910 CF₃ Br CH₂CHCH₂ CH₂CH₃ A-1911 CF₃ Br CH₂CHCH₂ CH₂CH₂CH₃ A-1912 CF₃ Br CH₂CHCH₂ CH₂CH₂OCH₃ A-1913 CF₃ Br CH₂CCH CH₃ A-1914 CF₃ Br CH₂CCH CH₂CH₃ A-1915 CF₃ Br CH₂CCH CH₂CH₂CH₃ A-1916 CF₃ Br CH₂CCH CH₂CH₂OCH₃ A-1917 CF₃ Br H CH₃ A-1918 CF₃ Br H CH₂CH₃ A-1919 CF₃ Br H CH₂CH₂CH₃ A-1920 CF₃ Br H CH₂CH₂OCH₃ A-1921 CF₃ CN CH₃ CH₃ A-1922 CF₃ CN CH₃ CH₂CH₃ A-1923 CF₃ CN CH₃ CH₂CH₂CH₃ A-1924 CF₃ CN CH₃ CH₂CH₂OCH₃ A-1925 CF₃ CN CH₂CH₃ CH₃ A-1926 CF₃ CN CH₂CH₃ CH₂CH₃ A-1927 CF₃ CN CH₂CH₃ CH₂CH₂CH₃ A-1928 CF₃ CN CH₂CH₃ CH₂CH₂OCH₃ A-1929 CF₃ CN CH₂OCH₃ CH₃ A-1930 CF₃ CN CH₂OCH₃ CH₂CH₃ A-1931 CF₃ CN CH₂OCH₃ CH₂CH₂CH₃ A-1932 CF₃ CN CH₂OCH₃ CH₂CH₂OCH₃ A-1933 CF₃ CN CH₂OCH₂CH₃ CH₃ A-1934 CF₃ CN CH₂OCH₂CH₃ CH₂CH₃ A-1935 CF₃ CN CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1936 CF₃ CN CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1937 CF₃ CN CH₂(CO)OCH₃ CH₃ A-1938 CF₃ CN CH₂(CO)OCH₃ CH₂CH₃ A-1939 CF₃ CN CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1940 CF₃ CN CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1941 CF₃ CN CH₂CHCH₂ CH₃ A-1942 CF₃ CN CH₂CHCH₂ CH₂CH₃ A-1943 CF₃ CN CH₂CHCH₂ CH₂CH₂CH₃ A-1944 CF₃ CN CH₂CHCH₂ CH₂CH₂OCH₃ A-1945 CF₃ CN CH₂CCH CH₃ A-1946 CF₃ CN CH₂CCH CH₂CH₃ A-1947 CF₃ CN CH₂CCH CH₂CH₂CH₃ A-1948 CF₃ CN CH₂CCH CH₂CH₂OCH₃ A-1949 CF₃ CN H CH₃ A-1950 CF₃ CN H CH₂CH₃ A-1951 CF₃ CN H CH₂CH₂CH₃ A-1952 CF₃ CN H CH₂CH₂OCH₃ A-1953 CF₃ CH₃ CH₃ CH₃ A-1954 CF₃ CH₃ CH₃ CH₂CH₃ A-1955 CF₃ CH₃ CH₃ CH₂CH₂CH₃ A-1956 CF₃ CH₃ CH₃ CH₂CH₂OCH₃ A-1957 CF₃ CH₃ CH₂CH₃ CH₃ A-1958 CF₃ CH₃ CH₂CH₃ CH₂CH₃ A-1959 CF₃ CH₃ CH₂CH₃ CH₂CH₂CH₃ A-1960 CF₃ CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-1961 CF₃ CH₃ CH₂OCH₃ CH₃ A-1962 CF₃ CH₃ CH₂OCH₃ CH₂CH₃ A-1963 CF₃ CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-1964 CF₃ CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1965 CF₃ CH₃ CH₂OCH₂CH₃ CH₃ A-1966 CF₃ CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-1967 CF₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-1968 CF₃ CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-1969 CF₃ CH₃ CH₂(CO)OCH₃ CH₃ A-1970 CF₃ CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-1971 CF₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-1972 CF₃ CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-1973 CF₃ CH₃ CH₂CHCH₂ CH₃ A-1974 CF₃ CH₃ CH₂CHCH₂ CH₂CH₃ A-1975 CF₃ CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-1976 CF₃ CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-1977 CF₃ CH₃ CH₂CCH CH₃ A-1978 CF₃ CH₃ CH₂CCH CH₂CH₃ A-1979 CF₃ CH₃ CH₂CCH CH₂CH₂CH₃ A-1980 CF₃ CH₃ CH₂CCH CH₂CH₂OCH₃ A-1981 CF₃ CH₃ H CH₃ A-1982 CF₃ CH₃ H CH₂CH₃ A-1983 CF₃ CH₃ H CH₂CH₂CH₃ A-1984 CF₃ CH₃ H CH₂CH₂OCH₃ A-1985 CF₃ CF₃ CH₃ CH₃ A-1986 CF₃ CF₃ CH₃ CH₂CH₃ A-1987 CF₃ CF₃ CH₃ CH₂CH₂CH₃ A-1988 CF₃ CF₃ CH₃ CH₂CH₂OCH₃ A-1989 CF₃ CF₃ CH₂CH₃ CH₃ A-1990 CF₃ CF₃ CH₂CH₃ CH₂CH₃ A-1991 CF₃ CF₃ CH₂CH₃ CH₂CH₂CH₃ A-1992 CF₃ CF₃ CH₂CH₃ CH₂CH₂OCH₃ A-1993 CF₃ CF₃ CH₂OCH₃ CH₃ A-1994 CF₃ CF₃ CH₂OCH₃ CH₂CH₃ A-1995 CF₃ CF₃ CH₂OCH₃ CH₂CH₂CH₃ A-1996 CF₃ CF₃ CH₂OCH₃ CH₂CH₂OCH₃ A-1997 CF₃ CF₃ CH₂OCH₂CH₃ CH₃ A-1998 CF₃ CF₃ CH₂OCH₂CH₃ CH₂CH₃ A-1999 CF₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-2000 CF₃ CF₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-2001 CF₃ CF₃ CH₂(CO)OCH₃ CH₃ A-2002 CF₃ CF₃ CH₂(CO)OCH₃ CH₂CH₃ A-2003 CF₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-2004 CF₃ CF₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-2005 CF₃ CF₃ CH₂CHCH₂ CH₃ A-2006 CF₃ CF₃ CH₂CHCH₂ CH₂CH₃ A-2007 CF₃ CF₃ CH₂CHCH₂ CH₂CH₂CH₃ A-2008 CF₃ CF₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-2009 CF₃ CF₃ CH₂CCH CH₃ A-2010 CF₃ CF₃ CH₂CCH CH₂CH₃ A-2011 CF₃ CF₃ CH₂CCH CH₂CH₂CH₃ A-2012 CF₃ CF₃ CH₂CCH CH₂CH₂OCH₃ A-2013 CF₃ CF₃ H CH₃ A-2014 CF₃ CF₃ H CH₂CH₃ A-2015 CF₃ CF₃ H CH₂CH₂CH₃ A-2016 CF₃ CF₃ H CH₂CH₂OCH₃ A-2017 CF₃ SO₂CH₃ CH₃ CH₃ A-2018 CF₃ SO₂CH₃ CH₃ CH₂CH₃ A-2019 CF₃ SO₂CH₃ CH₃ CH₂CH₂CH₃ A-2020 CF₃ SO₂CH₃ CH₃ CH₂CH₂OCH₃ A-2021 CF₃ SO₂CH₃ CH₂CH₃ CH₃ A-2022 CF₃ SO₂CH₃ CH₂CH₃ CH₂CH₃ A-2023 CF₃ SO₂CH₃ CH₂CH₃ CH₂CH₂CH₃ A-2024 CF₃ SO₂CH₃ CH₂CH₃ CH₂CH₂OCH₃ A-2025 CF₃ SO₂CH₃ CH₂OCH₃ CH₃ A-2026 CF₃ SO₂CH₃ CH₂OCH₃ CH₂CH₃ A-2027 CF₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂CH₃ A-2028 CF₃ SO₂CH₃ CH₂OCH₃ CH₂CH₂OCH₃ A-2029 CF₃ SO₂CH₃ CH₂OCH₂CH₃ CH₃ A-2030 CF₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₃ A-2031 CF₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂CH₃ A-2032 CF₃ SO₂CH₃ CH₂OCH₂CH₃ CH₂CH₂OCH₃ A-2033 CF₃ SO₂CH₃ CH₂(CO)OCH₃ CH₃ A-2034 CF₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₃ A-2035 CF₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂CH₃ A-2036 CF₃ SO₂CH₃ CH₂(CO)OCH₃ CH₂CH₂OCH₃ A-2037 CF₃ SO₂CH₃ CH₂CHCH₂ CH₃ A-2038 CF₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₃ A-2039 CF₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂CH₃ A-2040 CF₃ SO₂CH₃ CH₂CHCH₂ CH₂CH₂OCH₃ A-2041 CF₃ SO₂CH₃ CH₂CCH CH₃ A-2042 CF₃ SO₂CH₃ CH₂CCH CH₂CH₃ A-2043 CF₃ SO₂CH₃ CH₂CCH CH₂CH₂CH₃ A-2044 CF₃ SO₂CH₃ CH₂CCH CH₂CH₂OCH₃ A-2045 CF₃ SO₂CH₃ H CH₃ A-2046 CF₃ SO₂CH₃ H CH₂CH₃ A-2047 CF₃ SO₂CH₃ H CH₂CH₂CH₃ A-2048 CF₃ SO₂CH₃ H CH₂CH₂OCH₃

Examples of preferred compounds I.B, where X is CR², are the individual compounds compiled in Tables 16 to 210 below. Moreover, the meanings mentioned below for the individual variables in the Tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

Table 16 Compounds of formula I.B1 (I.B1-1.1-I.B1-1.2048) in which R² is H, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 17 Compounds of formula I.B1 (I.B1-2.1-II.B1-2.2048) in which R² is H, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 18 Compounds of formula I.B1 (I.B1-3.1-I.B1-3.2048) in which R² is H, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 19 Compounds of formula I.B1 (I.B1-4.1-I.B1-4.2048) in which R² is H, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 20 Compounds of formula I.B1 (I.B1-5.1-I.B1-5.2048) in which R² is H, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 21 Compounds of formula I.B1 (I.B1-6.1-I.B1-6.2048) in which R² is H, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 22 Compounds of formula I.B1 (I.B1-7.1-I.B1-7.2048) in which R² is H, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 23 Compounds of formula I.B1 (I.B1-8.1-I.B1-8.2048) in which R² is H, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 24 Compounds of formula I.B1 (I.B1-9.1-I.B1-9.2048) in which R² is H, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 25 Compounds of formula I.B1 (I.B1-10.1-I.B1-10.2048) in which R² is H, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 26 Compounds of formula I.B1 (I.B1-11.1-I.B1-11.2048) in which R² is H, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 27 Compounds of formula I.B1 (I.B1-12.1-I.B1-12.2048) in which R² is H, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 28 Compounds of formula I.B1 (I.B1-13.1-I.B1-13.2048) in which R² is H, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 29 Compounds of formula I.B1 (I.B1-14.1-I.B1-14.2048) in which R² is H, R⁴ is COH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 30 Compounds of formula I.B1 (I.B1-15.1-I.B1-15.2048) in which R² is H, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 31 Compounds of formula I.B2 (I.B2-1.1-I.B2-1.2048) in which R² is methyl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 32 Compounds of formula I.B2 (I.B2-2.1-II.B2-2.2048) in which R² is methyl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 33 Compounds of formula I.B2 (I.B2-3.1-I.B2-3.2048) in which R² is methyl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 34 Compounds of formula I.B2 (I.B2-4.1-I.B2-4.2048) in which R² is methyl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 35 Compounds of formula I.B2 (I.B2-5.1-I.B2-5.2048) in which R² is methyl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 36 Compounds of formula I.B2 (I.B2-6.1-I.B2-6.2048) in which R² is methyl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 37 Compounds of formula I.B2 (I.B2-7.1-I.B2-7.2048) in which R² is methyl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 38 Compounds of formula I.B2 (I.B2-8.1-I.B2-8.2048) in which R² is methyl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 39 Compounds of formula I.B2 (I.B2-9.1-I.B2-9.2048) in which R² is methyl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 40 Compounds of formula I.B2 (I.B2-10.1-I.B2-10.2048) in which R² is methyl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 41 Compounds of formula I.B2 (I.B2-11.1-I.B2-11.2048) in which R² is methyl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 42 Compounds of formula I.B2 (I.B2-12.1-I.B2-12.2048) in which R² is methyl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 43 Compounds of formula I.B2 (I.B2-13.1-I.B2-13.2048) in which R² is methyl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 44 Compounds of formula I.B2 (I.B2-14.1-I.B2-14.2048) in which R² is methyl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 45 Compounds of formula I.B2 (I.B2-15.1-I.B2-15.2048) in which R² is methyl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 46 Compounds of formula I.B3 (I.B3-1.1-I.B3-1.2048) in which R² is methylthio, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 47 Compounds of formula I.B3 (I.B3-2.1-II.B3-2.2048) in which R² is methylthio, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 48 Compounds of formula I.B3 (I.B3-3.1-I.B3-3.2048) in which R² is methylthio, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 49 Compounds of formula I.B3 (1.83-4.1-I.B3-4.2048) in which R² is methylthio, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 50 Compounds of formula I.B3 (I.B3-5.1-I.B3-5.2048) in which R² is methylthio, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 51 Compounds of formula I.B3 (I.B3-6.1-I.B3-6.2048) in which R² is methylthio, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 52 Compounds of formula I.B3 (I.B3-7.1-I.B3-7.2048) in which R² is methylthio, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 53 Compounds of formula I.B3 (I.B3-8.1-I.B3-8.2048) in which R² is methylthio, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 54 Compounds of formula I.B3 (I.B3-9.1-I.B3-9.2048) in which R² is methylthio, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 55 Compounds of formula I.B3 (I.B3-10.1-I.B3-10.2048) in which R² is methylthio, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 56 Compounds of formula I.B3 (I.B3-11.1-I.B3-11.2048) in which R² is methylthio, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 57 Compounds of formula I.B3 (I.B3-12.1-I.B3-12.2048) in which R² is methylthio, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 58 Compounds of formula I.B3 (I.B3-13.1-I.B3-13.2048) in which R² is methylthio, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 59 Compounds of formula I.B3 (I.B3-14.1-I.B3-14.2048) in which R² is methylthio, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 60 Compounds of formula I.B3 (I.B3-15.1-I.B3-15.2048) in which R² is methylthio, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 61 Compounds of formula I.B4 (I.B4-1.1-I.B4-1.2048) in which R² is ethylthio, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 62 Compounds of formula I.B4 (I.B4-2.1-II.B4-2.2048) in which R² is ethylthio, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 63 Compounds of formula I.B4 (I.B4-3.1-I.B4-3.2048) in which R² is ethylthio, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 64 Compounds of formula I.B4 (I.B4-4.1-I.B4-4.2048) in which R² is ethylthio, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 65 Compounds of formula I.B4 (I.B4-5.1-I.B4-5.2048) in which R² is ethylthio, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 66 Compounds of formula I.B4 (I.B4-6.1-I.B4-6.2048) in which R² is ethylthio, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 67 Compounds of formula I.B4 (I.B4-7.1-I.B4-7.2048) in which R² is ethylthio, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 68 Compounds of formula I.B4 (I.B4-8.1-I.B4-8.2048) in which R² is ethylthio, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 69 Compounds of formula I.B4 (I.B4-9.1-I.B4-9.2048) in which R² is ethylthio, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 70 Compounds of formula I.B4 (I.B4-10.1-I.B4-10.2048) in which R² is ethylthio, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 71 Compounds of formula I.B4 (I.B4-11.1-I.B4-11.2048) in which R² is ethylthio, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 72 Compounds of formula I.B4 (I.B4-12.1-I.B4-12.2048) in which R² is ethylthio, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 73 Compounds of formula I.B4 (I.B4-13.1-I.B4-13.2048) in which R² is ethylthio, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 74 Compounds of formula I.B4 (I.B4-14.1-I.B4-14.2048) in which R² is ethylthio, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 75 Compounds of formula I.B4 (I.B4-15.1-I.B4-15.2048) in which R² is ethylthio, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 76 Compounds of formula I.B5 (I.B5-1.1-I.B5-1.2048) in which R² is methylsulfonyl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 77 Compounds of formula I.B5 (I.B5-2.1-II.B5-2.2048) in which R² is methylsulfonyl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 78 Compounds of formula I.B5 (I.B5-3.1-I.B5-3.2048) in which R² is methylsulfonyl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 79 Compounds of formula I.B5 (I.B5-4.1-I.B5-4.2048) in which R² is methylsulfonyl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 80 Compounds of formula I.B5 (I.B5-5.1-I.B5-5.2048) in which R² is methylsulfonyl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 81 Compounds of formula I.B5 (I.B5-6.1-I.B5-6.2048) in which R² is methylsulfonyl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 82 Compounds of formula I.B5 (I.B5-7.1-I.B5-7.2048) in which R² is methylsulfonyl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 83 Compounds of formula I.B5 (I.B5-8.1-I.B5-8.2048) in which R² is methylsulfonyl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 84 Compounds of formula I.B5 (I.B5-9.1-I.B5-9.2048) in which R² is methylsulfonyl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 85 Compounds of formula I.B5 (I.B5-10.1-I.B5-10.2048) in which R² is methylsulfonyl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 86 Compounds of formula I.B5 (I.B5-11.1-I.B5-11.2048) in which R² is methylsulfonyl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 87 Compounds of formula I.B5 (I.B5-12.1-I.B5-12.2048) in which R² is methylsulfonyl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 88 Compounds of formula I.B5 (I.B5-13.1-I.B5-13.2048) in which R² is methylsulfonyl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 89 Compounds of formula I.B5 (I.B5-14.1-I.B5-14.2048) in which R² is methylsulfonyl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 90 Compounds of formula I.B5 (I.B5-15.1-I.B5-15.2048) in which R² is methylsulfonyl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 91 Compounds of formula I.B6 (I.B6-1.1-I.B6-1.2048) in which R² is ethylsulfonyl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 92 Compounds of formula I.B6 (I.B6-2.1-II.B6-2.2048) in which R² is ethylsulfonyl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 93 Compounds of formula I.B6 (I.B6-3.1-I.B6-3.2048) in which R² is ethylsulfonyl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 94 Compounds of formula I.B6 (I.B6-4.1-I.B6-4.2048) in which R² is ethylsulfonyl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 95 Compounds of formula I.B6 (I.B6-5.1-I.B6-5.2048) in which R² is ethylsulfonyl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 96 Compounds of formula I.B6 (I.B6-6.1-I.B6-6.2048) in which R² is ethylsulfonyl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 97 Compounds of formula I.B6 (I.B6-7.1-I.B6-7.2048) in which R² is ethylsulfonyl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 98 Compounds of formula I.B6 (I.B6-8.1-I.B6-8.2048) in which R² is ethylsulfonyl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 99 Compounds of formula I.B6 (I.B6-9.1-I.B6-9.2048) in which R² is ethylsulfonyl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 100 Compounds of formula I.B6 (I.B6-10.1-I.B6-10.2048) in which R² is ethylsulfonyl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 101 Compounds of formula I.B6 (I.B6-11.1-I.B6-11.2048) in which R² is ethylsulfonyl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 102 Compounds of formula I.B6 (I.B6-12.1-I.B6-12.2048) in which R² is ethylsulfonyl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 103 Compounds of formula I.B6 (I.B6-13.1-I.B6-13.2048) in which R² is ethylsulfonyl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 104 Compounds of formula I.B6 (I.B6-14.1-I.B6-14.2048) in which R² is ethylsulfonyl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 105 Compounds of formula I.B6 (I.B6-15.1-I.B6-15.2048) in which R² is ethylsulfonyl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 106 Compounds of formula I.B7 (I.B7-1.1-I.B7-1.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 107 Compounds of formula I.B7 (I.B7-2.1-II.B7-2.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 108 Compounds of formula I.B7 (I.B7-3.1-I.B7-3.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 109 Compounds of formula I.B7 (I.B7-4.1-I.B7-4.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 110 Compounds of formula I.B7 (I.B7-5.1-I.B7-5.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 111 Compounds of formula I.B7 (I.B7-6.1-I.B7-6.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 112 Compounds of formula I.B7 (I.B7-7.1-I.B7-7.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 113 Compounds of formula I.B7 (I.B7-8.1-I.B7-8.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 114 Compounds of formula I.B7 (I.B7-9.1-I.B7-9.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 115 Compounds of formula I.B7 (I.B7-10.1-I.B7-10.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 116 Compounds of formula I.B7 (I.B7-11.1-I.B7-11.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 117 Compounds of formula I.B7 (I.B7-12.1-I.B7-12.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 118 Compounds of formula I.B7 (I.B7-13.1-I.B7-13.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 119 Compounds of formula I.B7 (I.B7-14.1-I.B7-14.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 120 Compounds of formula I.B7 (I.B7-15.1-I.B7-15.2048) in which R² is trifluoromethyl-methoxymethyl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 121 Compounds of formula I.B8 (I.B8-1.1-I.B8-1.2048) in which R² is isoxazolin-3-yl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 122 Compounds of formula I.B8 (I.B8-2.1-II.B8-2.2048) in which R² is isoxazolin-3-yl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 123 Compounds of formula I.B8 (I.B8-3.1-I.B8-3.2048) in which R² is isoxazolin-3-yl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 124 Compounds of formula I.B8 (I.B8-4.1-I.B8-4.2048) in which R² is isoxazolin-3-yl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 125 Compounds of formula I.B8 (I.B8-5.1-I.B8-5.2048) in which R² is isoxazolin-3-yl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 126 Compounds of formula I.B8 (I.B8-6.1-I.B8-6.2048) in which R² is isoxazolin-3-yl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 127 Compounds of formula I.B8 (I.B8-7.1-I.B8-7.2048) in which R² is isoxazolin-3-yl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 128 Compounds of formula I.B8 (I.B8-8.1-I.B8-8.2048) in which R² is isoxazolin-3-yl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 129 Compounds of formula I.B8 (I.B8-9.1-I.B8-9.2048) in which R² is isoxazolin-3-yl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 130 Compounds of formula I.B8 (I.B8-10.1-I.B8-10.2048) in which R² is isoxazolin-3-yl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 131 Compounds of formula I.B8 (I.B8-11.1-I.B8-11.2048) in which R² is isoxazolin-3-yl, R⁴ is CN and R⁵ is F and the combination of Rt, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 132 Compounds of formula I.B8 (I.B8-12.1-I.B8-12.2048) in which R² is isoxazolin-3-yl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 133 Compounds of formula I.B8 (I.B8-13.1-I.B8-13.2048) in which R² is isoxazolin-3-yl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 134 Compounds of formula I.B8 (I.B8-14.1-I.B8-14.2048) in which R² is isoxazolin-3-yl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 135 Compounds of formula I.B8 (I.B8-15.1-I.B8-15.2048) in which R² is isoxazolin-3-yl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 136 Compounds of formula I.B9 (I.B9-1.1-I.B9-1.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 137 Compounds of formula I.B9 (I.B9-2.1-II.B9-2.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 138 Compounds of formula I.B9 (I.B9-3.1-I.B9-3.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 139 Compounds of formula I.B9 (I.B9-4.1-I.B9-4.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 140 Compounds of formula I.B9 (I.B9-5.1-I.B9-5.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 141 Compounds of formula I.B9 (I.B9-6.1-I.B9-6.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 142 Compounds of formula I.B9 (I.B9-7.1-I.B9-7.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 143 Compounds of formula I.B9 (I.B9-8.1-I.B9-8.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 144 Compounds of formula I.B9 (I.B9-9.1-I.B9-9.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 145 Compounds of formula I.B9 (I.B9-10.1-I.B9-10.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 146 Compounds of formula I.B9 (I.B9-11.1-I.B9-11.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 147 Compounds of formula I.B9 (I.B9-12.1-I.B9-12.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 148 Compounds of formula I.B9 (I.B9-13.1-I.B9-13.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 149 Compounds of formula I.B9 (I.B9-14.1-I.B9-14.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 150 Compounds of formula I.B9 (I.B9-15.1-I.B9-15.2048) in which R² is 5-methylisoxazolin-3-yl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 151 Compounds of formula I.B10 (I.B10-1.1-I.B10-1.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 152 Compounds of formula I.B10 (I.B10-2.1-II.B10-2.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 153 Compounds of formula I.B10 (I.B10-3.1-I.B10-3.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 154 Compounds of formula I.B10 (I.B10-4.1-I.B10-4.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 155 Compounds of formula I.B10 (I.B10-5.1-I.B10-5.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 156 Compounds of formula I.B10 (I.B10-6.1-I.B10-6.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 157 Compounds of formula I.B10 (I.B10-7.1-I.B10-7.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 158 Compounds of formula I.B10 (I.B10-8.1-I.B10-8.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 159 Compounds of formula I.B10 (I.B10-9.1-I.B10-9.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 160 Compounds of formula I.B10 (I.B10-10.1-I.B10-10.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 161 Compounds of formula I.B10 (I.B10-11.1-I.B10-11.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 162 Compounds of formula I.B10 (I.B10-12.1-I.B10-12.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 163 Compounds of formula I.B10 (I.B10-13.1-I.B10-13.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 164 Compounds of formula I.B10 (I.B10-14.1-I.B10-14.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 165 Compounds of formula I.B10 (I.B10-15.1-I.B10-15.2048) in which R² is 3-methylisoxazolin-5-yl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 166 Compounds of formula I.B11 (I.B11-1.1-I.B11-1.2048) in which R² is isoxazol-3-yl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 167 Compounds of formula I.B11 (I.B11-2.1-II.B11-2.2048) in which R² is isoxazol-3-yl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 168 Compounds of formula I.B11 (l.B11-3.1-I.B11-3.2048) in which R² is isoxazol-3-yl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 169 Compounds of formula I.B11 (I.B11-4.1-I.B11-4.2048) in which R² is isoxazol-3-yl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 170 Compounds of formula I.B11 (I.B11-5.1-I.B11-5.2048) in which R² is isoxazol-3-yl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 171 Compounds of formula I.B11 (I.B11-6.1-I.B11-6.2048) in which R² is isoxazol-3-yl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 172 Compounds of formula I.B11 (I.B11-7.1-I.B11-7.2048) in which R² is isoxazol-3-yl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 173 Compounds of formula I.B11 (I.B11-8.1-I.B11-8.2048) in which R² is isoxazol-3-yl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 174 Compounds of formula I.B11 (I.B11-9.1-I.B11-9.2048) in which R² is isoxazol-3-yl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 175 Compounds of formula I.B11 (I.B11-10.1-I.B11-10.2048) in which R² is isoxazol-3-yl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 176 Compounds of formula I.B11 (I.B11-11.1-I.B11-11.2048) in which R² is isoxazol-3-yl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 177 Compounds of formula I.B11 (I.B11-12.1-I.B11-12.2048) in which R² is isoxazol-3-yl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 178 Compounds of formula I.B11 (l.B11-13.1-I.B11-13.2048) in which R² is isoxazol-3-yl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 179 Compounds of formula I.B11 (I.B11-14.1-I.B11-14.2048) in which R² is isoxazol-3-yl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 180 Compounds of formula I.B11 (I.B11-15.1-I.B11-15.2048) in which R² is isoxazol-3-yl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 181 Compounds of formula I.B12 (I.B12-1.1-I.B12-1.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 182 Compounds of formula I.B12 (I.B12-2.1-II.B12-2.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 183 Compounds of formula I.B12 (I.B12-3.1-I.B12-3.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 184 Compounds of formula I.B12 (I.B12-4.1-I.B12-4.2048) in which R² is 5-methylisoxazol-3-yl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 185 Compounds of formula I.B12 (I.B12-5.1-I.B12-5.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 186 Compounds of formula I.B12 (I.B12-6.1-I.B12-6.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 187 Compounds of formula I.B12 (I.B12-7.1-I.B12-7.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 188 Compounds of formula I.B12 (I.B12-8.1-I.B12-8.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 189 Compounds of formula I.B12 (I.B12-9.1-I.B12-9.2048) in which R² is 5-methylisoxazol-3-yl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 190 Compounds of formula I.B12 (I.B12-10.1-I.B12-10.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 191 Compounds of formula I.B12 (I.B12-11.1-I.B12-11.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 192 Compounds of formula I.B12 (I.B12-12.1-I.B12-12.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 193 Compounds of formula I.B12 (I.B12-13.1-I.B12-13.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 194 Compounds of formula I.B12 (I.B12-14.1-I.B12-14.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 195 Compounds of formula I.B12 (l.B12-15.1-I.B12-15.2048) in which R² is 5-methyl-isoxazol-3-yl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 196 Compounds of formula I.B13 (I.B13-1.1-I.B13-1.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is H and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 197 Compounds of formula I.B13 (I.B13-2.1-II.B13-2.2048) in which R² is 3-methylisoxazol-5-yl, R⁴ is H and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 198 Compounds of formula I.B13 (I.B13-3.1-I.B13-3.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is H and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 199 Compounds of formula I.B13 (I.B13-4.1-I.B13-4.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is F and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 200 Compounds of formula I.B13 (I.B13-5.1-I.B13-5.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is F and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 201 Compounds of formula I.B13 (I.B13-6.1-I.B13-6.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is F and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 202 Compounds of formula I.B13 (I.B13-7.1-I.B13-7.2048) in which R² is 3-methylisoxazol-5-yl, R⁴ is Cl and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 203 Compounds of formula I.B13 (I.B13-8.1-I.B13-8.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is Cl and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 204 Compounds of formula I.B13 (I.B13-9.1-I.B13-9.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is Cl and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 205 Compounds of formula I.B13 (I.B13-10.1-I.B13-10.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is CN and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 206 Compounds of formula I.B13 (I.B13-11.1-I.B13-11.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is CN and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 207 Compounds of formula I.B13 (I.B13-12.1-I.B13-12.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is CN and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 208 Compounds of formula I.B13 (l.B13-13.1-I.B13-13.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is CH₃ and R⁵ is H and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 209 Compounds of formula I.B13 (I.B13-14.1-I.B13-14.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is CH₃ and R⁵ is F and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A; Table 210 Compounds of formula I.B13 (I.B13-15.1-I.B13-15.2048) in which R² is 3-methyl-isoxazol-5-yl, R⁴ is CH₃ and R⁵ is Cl and the combination of R¹, R³, R⁶ and R⁷ for a compound corresponds in each case to one row of Table A;

The compounds of formula I can be prepared by standard methods of organic chemistry, e.g. by the methods described hereinafter in schemes 1 to 4. The substituents, variables and indices in schemes 1 to 4 are as defined above for formula I, if not otherwise specified.

The compounds of formula I can be prepared analogous to Scheme 1 below.

N—R⁶-4-R⁷-1,2,4-triazol-3-amine compounds of formula III can be reacted with benzoyl derivatives of formula II to afford compounds of formula I. X is a leaving group, such as halogen, in particular Cl, an anhydride residue or an activated ester or activated amide residue. Especially in case of X being halogen the reaction is suitably carried out in the presence of a base. Suitable bases are for example carbonates, such as lithium, sodium or potassium carbonates, amines, such as trimethylamine or triethylamine, and basic N-heterocycles, such as pyridine, 2,6-dimethylpyridine or 2,4,6-trimethylpyridine. Suitable solvents are in particular aprotic solvents such as pentane, hexane, heptane, octane, cyclohexane, dichloromethane, chloroform, 1,2-dichlorethane, benzene, chlorobenzene, toluene, the xylenes, dichlorobenzene, trimethylbenzene, pyridine, 2,6-dimethylpyridine, 2,4,6-trimethylpyridine, acetonitrile, diethyl ether, tetrahydrofuran, 2-methyl tetrahydrofuran, methyl tert-butylether, 1,4-dioxane, N,N-dimethyl formamide, N-methyl pyrrolidinone or mixtures thereof. The starting materials are generally reacted with one another in equimolar or nearly equimolar amounts at a reaction temperature usually in the range of −20° C. to 100° C. and preferably in the range of −5° C. to 50° C.

Alternatively, compounds of formula I can also be prepared as shown in Scheme 2. Reaction of N—R⁶-4-R⁷-1,2,4-triazol-3-amine of formula III with a benzoic acid derivative of formula IV yields compound I. The reaction is preferably carried out in the presence of a suitable activating agent, which converts the carboxylic acid group of compound IV into an activated ester or an activated amide of formula II. For this purpose activating agents known in the art, such as 1,1′,carbonyldiimidazole (CDI), dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) or 1-propanephosphonic acid cyclic anhydride (PPAA) can be employed. The activated ester or amide can be formed, depending in particular on the specific activating agent used, either in situ by contacting compound IV with the activating agent in the presence of compound III, or in a separate step prior to the reaction with compound Ill. It may be advantageous, especially in cases where DCC, EDC and PPAA are used as activating agent, to include further additives in the activating reaction, such as hydroxybenzotriazole (HOBt), nitrophenol, pentafluorophenol, 2,4,5-trichlorophenol, N-hydroxysuccinimide or 4-Dimethylamino-pyridine (DMAP). It may further be advantageous to prepare the activated ester or amide in the presence of a base, for example a tertiary amine. The activated ester or amide is either in situ or subsequently reacted with the amine of formula III to afford the amide of formula I. The reaction normally takes place in anhydrous inert solvents, such as chlorinated hydrocarbons, e.g. dichloromethane or dichloroethane, ethers, e.g. tetrahydrofuran or 1,4-dioxane or carboxamides, e.g. N,N-dimethylformamide, N,N-dimethylacetamide or N-methylpyrrolidone. The reaction is ordinarily carried out at temperatures in the range from −20° C. to +25° C.

The compounds of formula II and their respective benzoic acid precursors of formula IV can be purchased or can be prepared by processes known in the art or disclosed in the literature, e.g. in WO 9746530, WO 9831676, WO 9831681, WO 2002/018352, WO 2000/003988, US 2007/0191335, U.S. Pat. No. 6,277,847.

Furthermore, compounds of formula I, where R⁶ is not hydrogen, can be obtained by treating N-(4-R⁷-1,2,4-triazol-3-yl)benzamides of formula V with, for example, alkylating agents such as alkyl halides according to Scheme 3.

The 4-R⁷-1,2,4-triazol-3-amine of formula III, where R⁷ is for example alkyl, can be prepared in a two steps manner (scheme 4). The first step consists of alkylating commercially available 5-nitro-1H-1,2,4-Triazole with an alkylating agent such as a alkyl halide or a dialkylsuflate. An example in the literature can be found in Chemistry in Heterocyclic Compounds, 2005, 41, 994. The second step is the reduction of the nitro group to the amino group. This reaction is done by known catalytic hydrogenation methods (Pd, Pt, Ni and Zn) or by Metal (Iron, Tin) reduction in acetic medium such as acetic acid or HCl. Some Literature references are quoted below: Synthesis 2003, 2001; Tetrahedron Letters 2005, 46, 2469; Tetrahedron Letters 1999, 40, 7855; Advanced Synthesis and Catalysis 2005, 347,217; Journal of the American Chemical Society 1944, 66, 1781 and Tetrahedron Letters 1984, 25, 839.

As a rule, the compounds of formula I including their stereoisomers, salts, tautomers and N-oxides, and their precursors in the synthesis process, can be prepared by the methods described above. If individual compounds can not be prepared via the above-described routes, they can be prepared by derivatization of other compounds of formula I or the respective precursor or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds of formula I can advantageously be prepared from other compounds of formula I by derivatization, e.g. by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like, or by customary modifications of the synthesis routes described.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration.

The compounds of formula I and their agriculturally suitable salts are useful as herbicides. They are useful as such or as an appropriately formulated composition. The herbicidal compositions comprising the compound I, in particular the preferred aspects thereof, control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and weed grasses in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.

Depending on the application method in question, the compounds of formula I, in particular the preferred aspects thereof, or compositions comprising them can additionally be employed in a further number of crop plants for eliminating unwanted plants. Examples of suitable crops are the following:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

The term “crop plants” also includes plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants whose genetic material has been modified in a manner which does not occur under natural conditions by crossing, mutations or natural recombination (i.e. reassembly of the genetic information). Here, in general, one or more genes are integrated into the genetic material of the plant to improve the properties of the plant.

Accordingly, the term “crop plants” also includes plants which, by breeding and genetic engineering, have acquired tolerance to certain classes of herbicides, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as, for example, sulfonylureas (EP-A-0257993, U.S. Pat. No. 5,013,659) or imidazolinones (see, for example, U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate 3-phosphate synthase (EPSPS) inhibitors, such as, for example, glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors, such as, for example, glufosinate (see, for example, EP-A-0242236, EP-A-242246), or oxynil herbicides (see, for example, U.S. Pat. No. 5,559,024).

Numerous crop plants, for example Clearfield® oilseed rape, tolerant to imidazolinones, for example imazamox, have been generated with the aid of classic breeding methods (mutagenesis). Crop plants such as soybeans, cotton, corn, beet and oilseed rape, resistant to glyphosate or glufosinate, which are available under the tradenames RoundupReady® (glyphosate) and Liberty Link® (glufosinate) have been generated with the aid of genetic engineering methods.

Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more toxins, for example those of the bacterial strain Bacillus ssp. Toxins which are produced by such genetically modified plants include, for example, insecticidal proteins of Bacillus spp., in particular B. thuringiensis, such as the endotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), for example VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, for example Photorhabdus spp. or Xenorhabdus spp.; toxins of animal organisms, for example wasp, spider or scorpion toxins; fungal toxins, for example from Streptomycetes; plant lectins, for example from peas or barley; agglutinins; proteinase inhibitors, for example trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors, ribosome-inactivating proteins (RIPs), for example ricin, corn-RIP, abrin, luffin, saporin or bryodin; steroid-metabolizing enzymes, for example 3-hydroxysteroid oxidase, ecdysteroid-IDP glycosyl transferase, cholesterol oxidase, ecdysone inhibitors, or HMG-CoA reductase; ion channel blockers, for example inhibitors of sodium channels or calcium channels; juvenile hormone esterase; receptors of the diuretic hormone (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases and glucanases. In the plants, these toxins may also be produced as pretoxins, hybrid proteins or truncated or otherwise modified proteins. Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701). Further examples of such toxins or genetically modified plants which produce these toxins are disclosed in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073. The methods for producing these genetically modified plants are known to the person skilled in the art and disclosed, for example, in the publications mentioned above. Numerous of the toxins mentioned above bestow, upon the plants by which they are produced, tolerance to pests from all taxonomic classes of arthropods, in particular to beetles (Coeleropta), dipterans (Diptera) and butterflies (Lepidoptera) and to nematodes (Nematoda).

Genetically modified plants which produce one or more genes coding for insecticidal toxins are described, for example, in the publications mentioned above, and some of them are commercially available, such as, for example, YieldGard® (corn varieties producing the toxin Cry1Ab), YieldGard® Plus (corn varieties which produce the toxins Cry1Ab and Cry3Bb1), Starlink® (corn varieties which produce the toxin Cry9c), Herculex® RW (corn varieties which produce the toxins Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton varieties which produce the toxin Cry1Ac), Bollgard® I (cotton varieties which produce the toxin Cry1Ac), Bollgard® II (cotton varieties which produce the toxins Cry1Ac and Cry2Ab2); VIPCOT® (cotton varieties which produce a VIP toxin); NewLeaf® (potato varieties which produce the toxin Cry3A); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Btl 1 (for example Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin Cry1Ab and the PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn varieties which produce a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn varieties which produce the toxin Cry3Bb1), IPC 531 from Monsanto Europe S.A., Belgium (cotton varieties which produce a modified version of the toxin Cry1Ac) and 1507 from Pioneer Overseas Corporation, Belgium (corn varieties which produce the toxin Cry1F and the PAT enzyme).

Accordingly, the term “crop plants” also includes plants which, with the aid of genetic engineering, produce one or more proteins which are more robust or have increased resistance to bacterial, viral or fungal pathogens, such as, for example, pathogenesis-related proteins (PR proteins, see EP-A 0 392 225), resistance proteins (for example potato varieties producing two resistance genes against Phytophthora infestans from the wild Mexican potato Solanum bulbocastanum) or T4 lysozyme (for example potato cultivars which, by producing this protein, are resistant to bacteria such as Erwinia amylvora).

Accordingly, the term “crop plants” also includes plants whose productivity has been improved with the aid of genetic engineering methods, for example by enhancing the potential yield (for example biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens.

The term “crop plants” also includes plants whose ingredients have been modified with the aid of genetic engineering methods in particular for improving human or animal diet, for example by oil plants producing health-promoting long-chain omega 3 fatty acids or monounsaturated omega 9 fatty acids (for example Nexera® oilseed rape).

The term “crop plants” also includes plants which have been modified with the aid of genetic engineering methods for improving the production of raw materials, for example by increasing the amylopectin content of potatoes (Amflora® potato).

Furthermore, it has been found that the compounds of formula I are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard, there have been found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for desiccating and/or defoliating plants using the compounds of formula I.

As desiccants, the compounds of formula I are particularly suitable for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.

Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the readily controllable defoliation of useful plants, in particular cotton.

Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.

The compounds of formula I, or the herbicidal compositions comprising the compounds of formula I, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting, or granules, by means of spraying, atomizing, dusting, spreading, watering or treatment of the seed or mixing with the seed. The use forms depend on the intended purpose; in each case, they should ensure the finest possible distribution of the active ingredients according to the invention.

The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I, and auxiliaries which are customary for the formulation of crop protection agents.

Examples of auxiliaries customary for the formulation of crop protection agents are inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, bactericides, antifreeze agents, antifoams, if appropriate colorants and, for seed formulations, adhesives.

Examples of thickeners (i.e. compounds which impart to the formulation modified flow properties, i.e. high viscosity in the state of rest and low viscosity in motion) are polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet minerals, such as Attaclay® (from Engelhardt).

Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

Bactericides can be added for stabilizing the aqueous herbicidal formulation. Examples of bactericides are bactericides based on diclorophen and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).

Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.

Examples of colorants are both sparingly water-soluble pigments and water-soluble dyes. Examples which may be mentioned are the dyes known under the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

Suitable inert auxiliaries are, for example, the following:

mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives; alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, for example amines such as N-methylpyrrolidone, and water.

Solid carriers are mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.

Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins, denatured proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types), polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers thereof.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active ingredients together with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of formula I or Ia, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier. Alternatively, it is also possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.

The concentrations of the compounds of formula I in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98% by weight, preferably 0.01 to 95% by weight of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The formulations or ready-to-use preparations may also comprise acids, bases or buffer systems, suitable examples being phosphoric acid or sulfuric acid, or urea or ammonia.

The compounds of formula I of the invention can for example be formulated as follows:

1. Products for Dilution with Water

A. Water-Soluble Concentrates

10 parts by weight of active compound are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants are added. The active compound dissolves upon dilution with water. This gives a formulation with an active compound content of 10% by weight.

B. Dispersible Concentrates

20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active compound content is 20% by weight.

C. Emulsifiable Concentrates

15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion. The formulation has an active compound content of 15% by weight.

D. Emulsions

25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (e.g. alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion. The formulation has an active compound content of 25% by weight.

E. Suspensions

In an agitated ball mill, 20 parts by weight of active compound are comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts by weight of water or an organic solvent to give a fine active compound suspension. Dilution with water gives a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.

F. Water-Dispersible Granules and Water-Soluble Granules

50 parts by weight of active compound are ground finely with addition of 50 parts by weight of dispersants and wetters and made into water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound. The formulation has an active compound content of 50% by weight.

G. Water-Dispersible Powders and Water-Soluble Powders

75 parts by weight of active compound are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.

H. Gel Formulations

In a ball mill, 20 parts by weight of active compound, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or of an organic solvent are ground to give a fine suspension. Dilution with water gives a stable suspension with active compound content of 20% by weight.

2. Products to be Applied Undiluted

I. Dusts

5 parts by weight of active compound are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dusting powder with an active compound content of 5% by weight.

J. Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are ground finely and associated with 99.5 parts by weight of carriers. Current methods here are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by weight.

K. ULV solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product to be applied undiluted with an active compound content of 10% by weight.

The compounds of formula I or the herbicidal compositions comprising them can be applied pre- or post-emergence, or together with the seed of a crop plant. It is also possible to apply the herbicidal compositions or active compounds by applying seed, pretreated with the herbicidal compositions or active compounds, of a crop plant. If the active compounds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).

In a further embodiment, the compounds of formula I or the herbicidal compositions can be applied by treating seed.

The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of formula I according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.

The term seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, cuttings and similar forms. Here, preferably, the term seed describes corns and seeds.

The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.

The rates of application of active compound are from 0.001 to 3.0, preferably 0.01 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage. To treat the seed, the compounds of formula I are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of formula I in combination with safeners. Safeners are chemical compounds which prevent or reduce damage to useful plants without substantially affecting the herbicidal action of the compounds of formula I on unwanted plants. They can be used both before sowing (for example in the treatment of seed, or on cuttings or seedlings) and before or after the emergence of the useful plant. The safeners and the compounds of formula I can be used simultaneously or in succession.

Suitable safeners are, for example, (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acids, phosphorothiolates and O-phenyl N-alkylcarbamates and their agriculturally useful salts and, provided that they have an acid function, their agriculturally useful derivatives, such as amides, esters and thioesters.

To broaden the activity spectrum and to obtain synergistic effects, the compounds of the formula I can be mixed and jointly applied with numerous representatives of other herbicidal or growth-regulating groups of active compounds or with safeners. Suitable mixing partners are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-(hetaroyl/aroyl)-1,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF₃-phenyl derivatives, carbamates, quinoline carboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivates, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and also phenylpyrazolines and isoxazolines and their derivatives.

Moreover, it may be useful to apply the compounds of formula I alone or in combination with other herbicides or else also mixed with further crop protection agents, jointly, for example with compositions for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions which are employed for alleviating nutritional and trace element deficiencies. Other additives such as nonphytotoxic oils and oil concentrates may also be added.

Examples of herbicides which can be used in combination with the N-(1,2,4-triazol-3-yl)arylcarboxamide compounds of formula I according to the present invention are:

b1) from the group of the lipid biosynthesis inhibitors:

alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;

b2) from the group of the ALS inhibitors:

amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribacsodium, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cloransulam, cloransulammethyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;

b3) from the group of the photosynthesis inhibitors:

ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromacil, bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquatdibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquatdimetilsulfate, pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumeton, terbuthylazine, terbutryn, thidiazuron and trietazine;

b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:

acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-[(isopropyl)methylsulfamoyl]benzamide (H-1; CAS 372137-35-4), ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (H-2; CAS 353292-31-6), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-3; CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-4; CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (H-5; CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H/pyrazole-1-carboxamide (H-6; CAS 45100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione, 1,5-dimethyl-6-thioxo-3-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-1,3,5-triazinane-2,4-dione, 2-(2,2,7-Trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione and 1-Methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione;

b5) from the group of the bleacher herbicides:

aclonifen, amitrol, beflubutamid, benzobicyclon, benzofenap, clomazone, diflufenican, fluridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, 4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (H-7; CAS 352010-68-5) and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (H-8; CAS 180608-33-7);

b6) from the group of the EPSP synthase inhibitors:

glyphosate, glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate);

b7) from the group of the glutamine synthase inhibitors:

bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;

b8) from the group of the DHP synthase inhibitors:

asulam;

b9) from the group of the mitose inhibitors:

amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, carbetamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam, thiazopyr and trifluralin;

b10) from the group of the VLCFA inhibitors:

acetochlor, alachlor, anilofos, butachlor, cafenstrole, dimethachlor, dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamid, piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchlor;

Compounds of the formula 2:

in which the variables have the following meanings: Y is phenyl or 5- or 6-membered heteroaryl as defined at the outset, which radicals may be substituted by one to three groups R^(aa); R²¹, R²², R²³, R²⁴ are H, halogen or C₁-C₄-alkyl; X is O or NH; N is 0 or 1.

Compounds of the formula 2 have in particular the following meanings:

where # denotes the bond to the skeleton of the molecule; and

R²¹, R²², R²³, R²⁴ are H, Cl, F or CH₃; R²⁵ is halogen, C₁-C₄-alkyl or C₁-C₄-haloalkyl; R²⁶ is C₁-C₄-alkyl; R²⁷ is halogen, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy; R²⁸ is H, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₁-C₄-haloalkoxy; M is 0, 1, 2 or 3; X is oxygen; N is 0 or 1.

Preferred compounds of the formula 2 have the following meanings:

R²¹ is H; R²², R²³ are F; R²⁴ is H or F; X is oxygen; N is 0 or 1.

Particularly preferred compounds of the formula 2 are:

3-[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethane-sulfonyl]-4-fldoro-5,5-dimethyl-4,5-dihydroisoxazole (2-1); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]fluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-2); 4-(4-fluoro-5,5-dimethyl-4, 5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-3); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)fluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-4); 4-(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl)-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-5); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-5,5-dimethyl-4,5-dihydroisoxazole (2-6); 4-[(5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)difluoromethyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-7); 3-{[5-(2,2-difluoroethoxy)-1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl]difluoromethanesulfonyl}-4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole (2-8); 4-[difluoro-(4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl)methyl]-2-methyl-5-trifluoromethyl-2H-[1,2,3]triazole (2-9);

b11) from the group of the cellulose biosynthesis inhibitors:

chlorthiamid, dichlobenil, flupoxam and isoxaben;

b12) from the group of the decoupler herbicides:

dinoseb, dinoterb and DNOC and its salts;

b13) from the group of the auxin herbicides:

2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts such as aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters;

b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium;

b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenolmethyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS 499223-49-3) and its salts and esters.

Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (H-11; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (H-12; R-29148, CAS 52836-31-4).

The active compounds of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart, 1995. Further herbicidally active compounds are known from WO 96/26202, WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459 and WO 2008/074991 and from W. Kramer et al. (ed.) “Modern Crop Protection Compounds”, Vol. 1, Wiley VCH, 2007 and the literature quoted therein.

The invention also relates to compositions in the form of a crop protection composition formulated as a 1-component composition comprising an active compound combination comprising at least one N-(1,2,4-triazol-3-yl)arylcarboxamide compound of the formula I and at least one further active compound, preferably selected from the active compounds of groups b1 to b15, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for crop protection compositions.

The invention also relates to compositions in the form of a crop protection composition formulated as a 2-component composition comprising a first component comprising at least one compound of the formula I, a solid or liquid carrier and/or one or more surfactants and a second component comprising at least one further active compound selected from the active compounds of groups b1 to b15, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for crop protection compositions.

In binary compositions comprising at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In binary compositions comprising at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

In ternary compositions comprising both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative parts by weight of the components A:B are generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1; and the weight ratio of the components B:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1. Preferably, the weight ratio of the components A+B to the component C is in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.

Examples of particularly preferred compositions according to the invention comprising in each case one individualized compound of the formula I and one mixing partner or a mixing partner combination are given in Table B below.

A further aspect of the invention relates to the compositions B-1 to B-1236 listed in Table B below, where in each case one row of Table B corresponds to a herbicidal composition comprising one of the compounds of formula I individualized in the above description (component 1) and the further active compound from groups b1) to b15) and/or safener C stated in each case in the row in question (component 2). The active compounds in the compositions described are in each case preferably present in synergistically effective amounts.

TABLE B Herbicide(s) B Safener C B-1 clodinafop-propargyl — B-2 cycloxydim — B-3 cyhalofop-butyl — B-4 fenoxaprop-P-ethyl — B-5 pinoxaden — B-6 profoxydim — B-7 tepraloxydim — B-8 tralkoxydim — B-9 esprocarb — B-10 prosulfocarb — B-11 thiobencarb — B-12 triallate — B-13 bensulfuron-methyl — B-14 bispyribac-sodium — B-15 cyclosulfamuron — B-16 flumetsulam — B-17 flupyrsulfuron-methyl-sodium — B-18 foramsulfuron — B-19 imazamox — B-20 imazapic — B-21 imazapyr — B-22 imazaquin — B-23 imazethapyr — B-24 imazosulfuron — B-25 iodosulfuron-methyl-sodium — B-26 mesosulfuron — B-27 nicosulfuron — B-28 penoxsulam — B-29 propoxycarbazone-sodium — B-30 pyrazosulfuron-ethyl — B-31 pyroxsulam — B-32 rimsulfuron — B-33 sulfosulfuron — B-34 thiencarbazone-methyl — B-35 tritosulfuron — B-36 2,4-D and its salts and esters — B-37 aminopyralid and its salts and esters — B-38 clopyralid and its salts and esters — B-39 dicamba and its salts and esters — B-40 fluroxypyr-meptyl — B-41 quinclorac — B-42 quinmerac — B-43 H-9 — B-44 diflufenzopyr — B-45 diflufenzopyr-sodium — B-46 clomazone — B-47 diflufenican — B-48 fluorochloridone — B-49 isoxaflutol — B-50 mesotrione — B-51 picolinafen — B-52 sulcotrione — B-53 tefuryltrione — B-54 tembotrione — B-55 topramezone — B-56 H-7 — B-57 atrazine — B-58 diuron — B-59 fluometuron — B-60 hexazinone — B-61 isoproturon — B-62 metribuzin — B-63 propanil — B-64 terbuthylazine — B-65 paraquat dichloride — B-66 flumioxazin — B-67 oxyfluorfen — B-68 saflufenacil — B-69 sulfentrazone — B-70 H-1 — B-71 H-2 — B-72 glyphosate — B-73 glyphosate-isopropylammonium — B-74 glyphosate-trimesium (sulfosate) — B-75 glufosinate — B-76 glufosinate-ammonium — B-77 pendimethalin — B-78 trifluralin — B-79 acetochlor — B-80 cafenstrole — B-81 dimethenamid-P — B-82 fentrazamide — B-83 flufenacet — B-84 mefenacet — B-85 metazachlor — B-86 metolachlor-S — B-87 pyroxasulfone — B-88 isoxaben — B-89 dymron — B-90 indanofan — B-91 oxaziclomefone — B-92 triaziflam — B-93 chlorotoluron — B-94 atrazine + H-1 — B-95 atrazine + glyphosate — B-96 atrazine + mesotrione — B-97 atrazine + nicosulfuron — B-98 atrazine + tembotrione — B-99 atrazine + topramezone — B-100 clomazone + glyphosate — B-101 diflufenican + clodinafop-propargyl — B-102 diflufenican + fenoxaprop-P-ethyl — B-103 diflufenican + flupyrsulfuron-methyl- — sodium B-104 diflufenican + glyphosate — B-105 diflufenican + mesosulfuron-methyl — B-106 diflufenican + pinoxaden — B-107 diflufenican + pyroxsulam — B-108 flumetsulam + glyphosate — B-109 flumioxazin + glyphosate — B-110 imazapic + glyphosate — B-111 imazethapyr + glyphosate — B-112 isoxaflutol + H-1 — B-113 isoxaflutol + glyphosate — B-114 metazachlor + H-1 — B-115 metazachlor + glyphosate — B-116 metazachlor + mesotrione — B-117 metazachlor + nicosulfuron — B-118 metazachlor + terbuthylazine — B-119 metazachlor + topramezone — B-120 metribuzin + glyphosate — B-121 pendimethalin + H-1 — B-122 pendimethalin + clodinafop-propargyl — B-123 pendimethalin + fenoxaprop-P-ethyl — B-124 pendimethalin + flupyrsulfuron-methyl- — sodium B-125 pendimethalin + glyphosate — B-126 pendimethalin + mesosulfuron-methyl — B-127 pendimethalin + mesotrione — B-128 pendimethalin + nicosulfuron — B-129 pendimethalin + pinoxaden — B-130 pendimethalin + pyroxsulam — B-131 pendimethalin + tembotrione — B-132 pendimethalin + topramezone — B-133 pyroxasulfone + tembotrione — B-134 pyroxasulfone + topramezone — B-135 sulfentrazone + glyphosate — B-136 terbuthylazine + H-1 — B-137 terbuthylazine + foramsulfuron — B-138 terbuthylazine + glyphosate — B-139 terbuthylazine + mesotrione — B-140 terbuthylazine + nicosulfuron — B-141 terbuthylazine + tembotrione — B-142 terbuthylazine + topramezone — B-143 trifluralin + glyphosate — B-144 — benoxacor B-145 — cloquintocet B-146 — cyprosulfamide B-147 — dichlormid B-148 — fenchlorazole B-149 — isoxadifen B-150 — mefenpyr B-151 — H-11 B-152 — H-12 B-153 clodinafop-propargyl benoxacor B-154 cycloxydim benoxacor B-155 cyhalofop-butyl benoxacor B-156 fenoxaprop-P-ethyl benoxacor B-157 pinoxaden benoxacor B-158 profoxydim benoxacor B-159 tepraloxydim benoxacor B-160 tralkoxydim benoxacor B-161 esprocarb benoxacor B-162 prosulfocarb benoxacor B-163 thiobencarb benoxacor B-164 triallate benoxacor B-165 bensulfuron-methyl benoxacor B-166 bispyribac-sodium benoxacor B-167 cyclosulfamuron benoxacor B-168 flumetsulam benoxacor B-169 flupyrsulfuron-methyl-sodium benoxacor B-170 foramsulfuron benoxacor B-171 imazamox benoxacor B-172 imazapic benoxacor B-173 imazapyr benoxacor B-174 imazaquin benoxacor B-175 imazethapyr benoxacor B-176 imazosulfuron benoxacor B-177 iodosulfuron-methyl-sodium benoxacor B-178 mesosulfuron benoxacor B-179 nicosulfuron benoxacor B-180 penoxsulam benoxacor B-181 propoxycarbazone-sodium benoxacor B-182 pyrazosulfuron-ethyl benoxacor B-183 pyroxsulam benoxacor B-184 rimsulfuron benoxacor B-185 sulfosulfuron benoxacor B-186 thiencarbazone-methyl benoxacor B-187 tritosulfuron benoxacor B-188 2,4-D and its salts and esters benoxacor B-189 aminopyralid and its salts and esters benoxacor B-190 clopyralid and its salts and esters benoxacor B-191 dicamba and its salts and esters benoxacor B-192 fluroxypyr-meptyl benoxacor B-193 quinclorac benoxacor B-194 quinmerac benoxacor B-195 H-9 benoxacor B-196 diflufenzopyr benoxacor B-197 diflufenzopyr-sodium benoxacor B-198 clomazone benoxacor B-199 diflufenican benoxacor B-200 fluorochloridone benoxacor B-201 isoxaflutol benoxacor B-202 mesotrione benoxacor B-203 picolinafen benoxacor B-204 sulcotrione benoxacor B-205 tefuryltrione benoxacor B-206 tembotrione benoxacor B-207 topramezone benoxacor B-208 H-7 benoxacor B-209 atrazine benoxacor B-210 diuron benoxacor B-211 fluometuron benoxacor B-212 hexazinone benoxacor B-213 isoproturon benoxacor B-214 metribuzin benoxacor B-215 propanil benoxacor B-216 terbuthylazine benoxacor B-217 paraquat dichloride benoxacor B-218 flumioxazin benoxacor B-219 oxyfluorfen benoxacor B-220 saflufenacil benoxacor B-221 sulfentrazone benoxacor B-222 H-1 benoxacor B-223 H-2 benoxacor B-224 glyphosate benoxacor B-225 glyphosate-isopropylammonium benoxacor B-226 glyphosate-trimesium (sulfosate) benoxacor B-227 glufosinate benoxacor B-228 glufosinate-ammonium benoxacor B-229 pendimethalin benoxacor B-230 trifluralin benoxacor B-231 acetochlor benoxacor B-232 cafenstrole benoxacor B-233 dimethenamid-P benoxacor B-234 fentrazamide benoxacor B-235 flufenacet benoxacor B-236 mefenacet benoxacor B-237 metazachlor benoxacor B-238 metolachlor-S benoxacor B-239 pyroxasulfone benoxacor B-240 isoxaben benoxacor B-241 dymron benoxacor B-242 indanofan benoxacor B-243 oxaziclomefone benoxacor B-244 triaziflam benoxacor B-245 atrazine + H-1 benoxacor B-246 atrazine + glyphosate benoxacor B-247 atrazine + mesotrione benoxacor B-248 atrazine + nicosulfuron benoxacor B-249 atrazine + tembotrione benoxacor B-250 atrazine + topramezone benoxacor B-251 clomazone + glyphosate benoxacor B-252 diflufenican + clodinafop-propargyl benoxacor B-253 diflufenican + fenoxaprop-P-ethyl benoxacor B-254 diflufenican + flupyrsulfuron-methyl- benoxacor sodium B-255 diflufenican + glyphosate benoxacor B-256 diflufenican + mesosulfuron-methyl benoxacor B-257 diflufenican + pinoxaden benoxacor B-258 diflufenican + pyroxsulam benoxacor B-259 flumetsulam + glyphosate benoxacor B-260 flumioxazin + glyphosate benoxacor B-261 imazapic + glyphosate benoxacor B-262 imazethapyr + glyphosate benoxacor B-263 isoxaflutol + H-1 benoxacor B-264 isoxaflutol + glyphosate benoxacor B-265 metazachlor + H-1 benoxacor B-266 metazachlor + glyphosate benoxacor B-267 metazachlor + mesotrione benoxacor B-268 metazachlor + nicosulfuron benoxacor B-269 metazachlor + terbuthylazine benoxacor B-270 metazachlor + topramezone benoxacor B-271 metribuzin + glyphosate benoxacor B-272 pendimethalin + H-1 benoxacor B-273 pendimethalin + clodinafop-propargyl benoxacor B-274 pendimethalin + fenoxaprop-P-ethyl benoxacor B-275 pendimethalin + flupyrsulfuron-methyl- benoxacor sodium B-276 pendimethalin + glyphosate benoxacor B-277 pendimethalin + mesosulfuron-methyl benoxacor B-278 pendimethalin + mesotrione benoxacor B-279 pendimethalin + nicosulfuron benoxacor B-280 pendimethalin + pinoxaden benoxacor B-281 pendimethalin + pyroxsulam benoxacor B-282 pendimethalin + tembotrione benoxacor B-283 pendimethalin + topramezone benoxacor B-284 pyroxasulfone + tembotrione benoxacor B-285 pyroxasulfone + topramezone benoxacor B-286 sulfentrazone + glyphosate benoxacor B-287 terbuthylazine + H-1 benoxacor B-288 terbuthylazine + foramsulfuron benoxacor B-289 terbuthylazine + glyphosate benoxacor B-290 terbuthylazine + mesotrione benoxacor B-291 terbuthylazine + nicosulfuron benoxacor B-292 terbuthylazine + tembotrione benoxacor B-293 terbuthylazine + topramezone benoxacor B-294 trifluralin + glyphosate benoxacor B-295 clodinafop-propargyl cloquintocet B-296 cycloxydim cloquintocet B-297 cyhalofop-butyl cloquintocet B-298 fenoxaprop-P-ethyl cloquintocet B-299 pinoxaden cloquintocet B-300 profoxydim cloquintocet B-301 tepraloxydim cloquintocet B-302 tralkoxydim cloquintocet B-303 esprocarb cloquintocet B-304 prosulfocarb cloquintocet B-305 thiobencarb cloquintocet B-306 triallate cloquintocet B-307 bensulfuron-methyl cloquintocet B-308 bispyribac-sodium cloquintocet B-309 cyclosulfamuron cloquintocet B-310 flumetsulam cloquintocet B-311 flupyrsulfuron-methyl-sodium cloquintocet B-312 foramsulfuron cloquintocet B-313 imazamox cloquintocet B-314 imazapic cloquintocet B-315 imazapyr cloquintocet B-316 imazaquin cloquintocet B-317 imazethapyr cloquintocet B-318 imazosulfuron cloquintocet B-319 iodosulfuron-methyl-sodium cloquintocet B-320 mesosulfuron cloquintocet B-321 nicosulfuron cloquintocet B-322 penoxsulam cloquintocet B-323 propoxycarbazone-sodium cloquintocet B-324 pyrazosulfuron-ethyl cloquintocet B-325 pyroxsulam cloquintocet B-326 rimsulfuron cloquintocet B-327 sulfosulfuron cloquintocet B-328 thiencarbazone-methyl cloquintocet B-329 tritosulfuron cloquintocet B-330 2,4-D and its salts and esters cloquintocet B-331 aminopyralid and its salts and esters cloquintocet B-332 clopyralid and its salts and esters cloquintocet B-333 dicamba and its salts and esters cloquintocet B-334 fluroxypyr-meptyl cloquintocet B-335 quinclorac cloquintocet B-336 quinmerac cloquintocet B-337 H-9 cloquintocet B-338 diflufenzopyr cloquintocet B-339 diflufenzopyr-sodium cloquintocet B-340 clomazone cloquintocet B-341 diflufenican cloquintocet B-342 fluorochloridone cloquintocet B-343 isoxaflutol cloquintocet B-344 mesotrione cloquintocet B-345 picolinafen cloquintocet B-346 sulcotrione cloquintocet B-347 tefuryltrione cloquintocet B-348 tembotrione cloquintocet B-349 topramezone cloquintocet B-350 H-7 cloquintocet B-351 atrazine cloquintocet B-352 diuron cloquintocet B-353 fluometuron cloquintocet B-354 hexazinone cloquintocet B-355 isoproturon cloquintocet B-356 metribuzin cloquintocet B-357 propanil cloquintocet B-358 terbuthylazine cloquintocet B-359 paraquat dichloride cloquintocet B-360 flumioxazin cloquintocet B-361 oxyfluorfen cloquintocet B-362 saflufenacil cloquintocet B-363 sulfentrazone cloquintocet B-364 H-1 cloquintocet B-365 H-2 cloquintocet B-366 glyphosate cloquintocet B-367 glyphosate-isopropylammonium cloquintocet B-368 glyphosate-trimesium (sulfosate) cloquintocet B-369 glufosinate cloquintocet B-370 glufosinate-ammonium cloquintocet B-371 pendimethalin cloquintocet B-372 trifluralin cloquintocet B-373 acetochlor cloquintocet B-374 cafenstrole cloquintocet B-375 dimethenamid-P cloquintocet B-376 fentrazamide cloquintocet B-377 flufenacet cloquintocet B-378 mefenacet cloquintocet B-379 metazachlor cloquintocet B-380 metolachlor-S cloquintocet B-381 pyroxasulfone cloquintocet B-382 isoxaben cloquintocet B-383 dymron cloquintocet B-384 indanofan cloquintocet B-385 oxaziclomefone cloquintocet B-386 triaziflam cloquintocet B-387 atrazine + H-1 cloquintocet B-388 atrazine + glyphosate cloquintocet B-389 atrazine + mesotrione cloquintocet B-390 atrazine + nicosulfuron cloquintocet B-391 atrazine + tembotrione cloquintocet B-392 atrazine + topramezone cloquintocet B-393 clomazone + glyphosate cloquintocet B-394 diflufenican + clodinafop-propargyl cloquintocet B-395 diflufenican + fenoxaprop-p-ethyl cloquintocet B-396 diflufenican + flupyrsulfuron-methyl- cloquintocet sodium B-397 diflufenican + glyphosate cloquintocet B-398 diflufenican + mesosulfuron-methyl cloquintocet B-399 diflufenican + pinoxaden cloquintocet B-400 diflufenican + pyroxsulam cloquintocet B-401 flumetsulam + glyphosate cloquintocet B-402 flumioxazin + glyphosate cloquintocet B-403 imazapic + glyphosate cloquintocet B-404 imazethapyr + glyphosate cloquintocet B-405 isoxaflutol + H-1 cloquintocet B-406 isoxaflutol + glyphosate cloquintocet B-407 metazachlor + H-1 cloquintocet B-408 metazachlor + glyphosate cloquintocet B-409 metazachlor + mesotrione cloquintocet B-410 metazachlor + nicosulfuron cloquintocet B-411 metazachlor + terbuthylazine cloquintocet B-412 metazachlor + topramezone cloquintocet B-413 metribuzin + glyphosate cloquintocet B-414 pendimethalin + H-1 cloquintocet B-415 pendimethalin + clodinafop-propargyl cloquintocet B-416 pendimethalin + fenoxaprop-P-ethyl cloquintocet B-417 pendimethalin + flupyrsulfuron-methyl- cloquintocet sodium B-418 pendimethalin + glyphosate cloquintocet B-419 pendimethalin + mesosulfuron-methyl cloquintocet B-420 pendimethalin + mesotrione cloquintocet B-421 pendimethalin + nicosulfuron cloquintocet B-422 pendimethalin + pinoxaden cloquintocet B-423 pendimethalin + pyroxsulam cloquintocet B-424 pendimethalin + tembotrione cloquintocet B-425 pendimethalin + topramezone cloquintocet B-426 pyroxasulfone + tembotrione cloquintocet B-427 pyroxasulfone + topramezone cloquintocet B-428 sulfentrazone + glyphosate cloquintocet B-429 terbuthylazine + H-1 cloquintocet B-430 terbuthylazine + foramsulfuron cloquintocet B-431 terbuthylazine + glyphosate cloquintocet B-432 terbuthylazine + mesotrione cloquintocet B-433 terbuthylazine + nicosulfuron cloquintocet B-434 terbuthylazine + tembotrione cloquintocet B-435 terbuthylazine + topramezone cloquintocet B-436 trifluralin + glyphosate cloquintocet B-437 clodinafop-propargyl dichlormid B-438 cycloxydim dichlormid B-439 cyhalofop-butyl dichlormid B-440 fenoxaprop-P-ethyl dichlormid B-441 pinoxaden dichlormid B-442 profoxydim dichlormid B-443 tepraloxydim dichlormid B-444 tralkoxydim dichlormid B-445 esprocarb dichlormid B-446 prosulfocarb dichlormid B-447 thiobencarb dichlormid B-448 triallate dichlormid B-449 bensulfuron-methyl dichlormid B-450 bispyribac-sodium dichlormid B-451 cyclosulfamuron dichlormid B-452 flumetsulam dichlormid B-453 flupyrsulfuron-methyl-sodium dichlormid B-454 foramsulfuron dichlormid B-455 imazamox dichlormid B-456 imazapic dichlormid B-457 imazapyr dichlormid B-458 imazaquin dichlormid B-459 imazethapyr dichlormid B-460 imazosulfuron dichlormid B-461 iodosulfuron-methyl-sodium dichlormid B-462 mesosulfuron dichlormid B-463 nicosulfuron dichlormid B-464 penoxsulam dichlormid B-465 propoxycarbazone-sodium dichlormid B-466 pyrazosulfuron-ethyl dichlormid B-467 pyroxsulam dichlormid B-468 rimsulfuron dichlormid B-469 sulfosulfuron dichlormid B-470 thiencarbazone-methyl dichlormid B-471 tritosulfuron dichlormid B-472 2,4-D and its salts and esters dichlormid B-473 aminopyralid and its salts and esters dichlormid B-474 clopyralid and its salts and esters dichlormid B-475 dicamba and its salts and esters dichlormid B-476 fluroxypyr-meptyl dichlormid B-477 quinclorac dichlormid B-478 quinmerac dichlormid B-479 H-9 dichlormid B-480 diflufenzopyr dichlormid B-481 diflufenzopyr-sodium dichlormid B-482 clomazone dichlormid B-483 diflufenican dichlormid B-484 fluorochloridone dichlormid B-485 isoxaflutol dichlormid B-486 mesotrione dichlormid B-487 picolinafen dichlormid B-488 sulcotrione dichlormid B-489 tefuryltrione dichlormid B-490 tembotrione dichlormid B-491 topramezone dichlormid B-492 H-7 dichlormid B-493 atrazine dichlormid B-494 diuron dichlormid B-495 fluometuron dichlormid B-496 hexazinone dichlormid B-497 isoproturon dichlormid B-498 metribuzin dichlormid B-499 propanil dichlormid B-500 terbuthylazine dichlormid B-501 paraquat dichloride dichlormid B-502 flumioxazin dichlormid B-503 oxyfluorfen dichlormid B-504 saflufenacil dichlormid B-505 sulfentrazone dichlormid B-506 H-1 dichlormid B-507 H-2 dichlormid B-508 glyphosate dichlormid B-509 glyphosate-isopropylammonium dichlormid B-510 glyphosate-trimesium (sulfosate) dichlormid B-511 glufosinate dichlormid B-512 glufosinate-ammonium dichlormid B-513 pendimethalin dichlormid B-514 trifluralin dichlormid B-515 acetochlor dichlormid B-516 cafenstrole dichlormid B-517 dimethenamid-P dichlormid B-518 fentrazamide dichlormid B-519 flufenacet dichlormid B-520 mefenacet dichlormid B-521 metazachlor dichlormid B-522 metolachlor-S dichlormid B-523 pyroxasulfone dichlormid B-524 isoxaben dichlormid B-525 dymron dichlormid B-526 indanofan dichlormid B-527 oxaziclomefone dichlormid B-528 triaziflam dichlormid B-529 atrazine + H-1 dichlormid B-530 atrazine + glyphosate dichlormid B-531 atrazine + mesotrione dichlormid B-532 atrazine + nicosulfuron dichlormid B-533 atrazine + tembotrione dichlormid B-534 atrazine + topramezone dichlormid B-535 clomazone + glyphosate dichlormid B-536 diflufenican + clodinafop-propargyl dichlormid B-537 diflufenican + fenoxaprop-p-ethyl dichlormid B-538 diflufenican + flupyrsulfuron-methyl- dichlormid sodium B-539 diflufenican + glyphosate dichlormid B-540 diflufenican + mesosulfuron-methyl dichlormid B-541 diflufenican + pinoxaden dichlormid B-542 diflufenican + pyroxsulam dichlormid B-543 flumetsulam + glyphosate dichlormid B-544 flumioxazin + glyphosate dichlormid B-545 imazapic + glyphosate dichlormid B-546 imazethapyr + glyphosate dichlormid B-547 isoxaflutol + H-1 dichlormid B-548 isoxaflutol + glyphosate dichlormid B-549 metazachlor + H-1 dichlormid B-550 metazachlor + glyphosate dichlormid B-551 metazachlor + mesotrione dichlormid B-552 metazachlor + nicosulfuron dichlormid B-553 metazachlor + terbuthylazine dichlormid B-554 metazachlor + topramezone dichlormid B-555 metribuzin + glyphosate dichlormid B-556 pendimethalin + H-1 dichlormid B-557 pendimethalin + clodinafop-propargyl dichlormid B-558 pendimethalin + fenoxaprop-P-ethyl dichlormid B-559 pendimethalin + flupyrsulfuron-methyl- dichlormid sodium B-560 pendimethalin + glyphosate dichlormid B-561 pendimethalin + mesosulfuron-methyl dichlormid B-562 pendimethalin + mesotrione dichlormid B-563 pendimethalin + nicosulfuron dichlormid B-564 pendimethalin + pinoxaden dichlormid B-565 pendimethalin + pyroxsulam dichlormid B-566 pendimethalin + tembotrione dichlormid B-567 pendimethalin + topramezone dichlormid B-568 pyroxasulfone + tembotrione dichlormid B-569 pyroxasulfone + topramezone dichlormid B-570 sulfentrazone + glyphosate dichlormid B-571 terbuthylazine + H-1 dichlormid B-572 terbuthylazine + foramsulfuron dichlormid B-573 terbuthylazine + glyphosate dichlormid B-574 terbuthylazine + mesotrione dichlormid B-575 terbuthylazine + nicosulfuron dichlormid B-576 terbuthylazine + tembotrione dichlormid B-577 terbuthylazine + topramezone dichlormid B-578 trifluralin + glyphosate dichlormid B-579 clodinafop-propargyl fenchlorazole B-580 cycloxydim fenchlorazole B-581 cyhalofop-butyl fenchlorazole B-582 fenoxaprop-P-ethyl fenchlorazole B-583 pinoxaden fenchlorazole B-584 profoxydim fenchlorazole B-585 tepraloxydim fenchlorazole B-586 tralkoxydim fenchlorazole B-587 esprocarb fenchlorazole B-588 prosulfocarb fenchlorazole B-589 thiobencarb fenchlorazole B-590 triallate fenchlorazole B-591 bensulfuron-methyl fenchlorazole B-592 bispyribac-sodium fenchlorazole B-593 cyclosulfamuron fenchlorazole B-594 flumetsulam fenchlorazole B-595 flupyrsulfuron-methyl-sodium fenchlorazole B-596 foramsulfuron fenchlorazole B-597 imazamox fenchlorazole B-598 imazapic fenchlorazole B-599 imazapyr fenchlorazole B-600 imazaquin fenchlorazole B-601 imazethapyr fenchlorazole B-602 imazosulfuron fenchlorazole B-603 iodosulfuron-methyl-sodium fenchlorazole B-604 mesosulfuron fenchlorazole B-605 nicosulfuron fenchlorazole B-606 penoxsulam fenchlorazole B-607 propoxycarbazone-sodium fenchlorazole B-608 pyrazosulfuron-ethyl fenchlorazole B-609 pyroxsulam fenchlorazole B-610 rimsulfuron fenchlorazole B-611 sulfosulfuron fenchlorazole B-612 thiencarbazone-methyl fenchlorazole B-613 tritosulfuron fenchlorazole B-614 2,4-D and its salts and esters fenchlorazole B-615 aminopyralid and its salts and esters fenchlorazole B-616 clopyralid and its salts and esters fenchlorazole B-617 dicamba and its salts and esters fenchlorazole B-618 fluroxypyr-meptyl fenchlorazole B-619 quinclorac fenchlorazole B-620 quinmerac fenchlorazole B-621 H-9 fenchlorazole B-622 diflufenzopyr fenchlorazole B-623 diflufenzopyr-sodium fenchlorazole B-624 clomazone fenchlorazole B-625 diflufenican fenchlorazole B-626 fluorochloridone fenchlorazole B-627 isoxaflutol fenchlorazole B-628 mesotrione fenchlorazole B-629 picolinafen fenchlorazole B-630 sulcotrione fenchlorazole B-631 tefuryltrione fenchlorazole B-632 tembotrione fenchlorazole B-633 topramezone fenchlorazole B-634 H-7 fenchlorazole B-635 atrazine fenchlorazole B-636 diuron fenchlorazole B-637 fluometuron fenchlorazole B-638 hexazinone fenchlorazole B-639 isoproturon fenchlorazole B-640 metribuzin fenchlorazole B-641 propanil fenchlorazole B-642 terbuthylazine fenchlorazole B-643 paraquat dichloride fenchlorazole B-644 flumioxazin fenchlorazole B-645 oxyfluorfen fenchlorazole B-646 saflufenacil fenchlorazole B-647 sulfentrazone fenchlorazole B-648 H-1 fenchlorazole B-649 H-2 fenchlorazole B-650 glyphosate fenchlorazole B-651 glyphosate-isopropylammonium fenchlorazole B-652 glyphosate-trimesium (sulfosate) fenchlorazole B-653 glufosinate fenchlorazole B-654 glufosinate-ammonium fenchlorazole B-655 pendimethalin fenchlorazole B-656 trifluralin fenchlorazole B-657 acetochlor fenchlorazole B-658 cafenstrole fenchlorazole B-659 dimethenamid-P fenchlorazole B-660 fentrazamide fenchlorazole B-661 flufenacet fenchlorazole B-662 mefenacet fenchlorazole B-663 metazachlor fenchlorazole B-664 metolachlor-S fenchlorazole B-665 pyroxasulfone fenchlorazole B-666 isoxaben fenchlorazole B-667 dymron fenchlorazole B-668 indanofan fenchlorazole B-669 oxaziclomefone fenchlorazole B-670 triaziflam fenchlorazole B-671 atrazine + H-1 fenchlorazole B-672 atrazine + glyphosate fenchlorazole B-673 atrazine + mesotrione fenchlorazole B-674 atrazine + nicosulfuron fenchlorazole B-675 atrazine + tembotrione fenchlorazole B-676 atrazine + topramezone fenchlorazole B-677 clomazone + glyphosate fenchlorazole B-678 diflufenican + clodinafop-propargyl fenchlorazole B-679 diflufenican + fenoxaprop-P-ethyl fenchlorazole B-680 diflufenican + flupyrsulfuron-methyl- fenchlorazole sodium B-681 diflufenican + glyphosate fenchlorazole B-682 diflufenican + mesosulfuron-methyl fenchlorazole B-683 diflufenican + pinoxaden fenchlorazole B-684 diflufenican + pyroxsulam fenchlorazole B-685 flumetsulam + glyphosate fenchlorazole B-686 flumioxazin + glyphosate fenchlorazole B-687 imazapic + glyphosate fenchlorazole B-688 imazethapyr + glyphosate fenchlorazole B-689 isoxaflutol + H-1 fenchlorazole B-690 isoxaflutol + glyphosate fenchlorazole B-691 metazachlor + H-1 fenchlorazole B-692 metazachlor + glyphosate fenchlorazole B-693 metazachlor + mesotrione fenchlorazole B-694 metazachlor + nicosulfuron fenchlorazole B-695 metazachlor + terbuthylazine fenchlorazole B-696 metazachlor + topramezone fenchlorazole B-697 metribuzin + glyphosate fenchlorazole B-698 pendimethalin + H-1 fenchlorazole B-699 pendimethalin + clodinafop-propargyl fenchlorazole B-700 pendimethalin + fenoxaprop-P-ethyl fenchlorazole B-701 pendimethalin + flupyrsulfuron-methyl- fenchlorazole sodium B-702 pendimethalin + glyphosate fenchlorazole B-703 pendimethalin + mesosulfuron-methyl fenchlorazole B-704 pendimethalin + mesotrione fenchlorazole B-705 pendimethalin + nicosulfuron fenchlorazole B-706 pendimethalin + pinoxaden fenchlorazole B-707 pendimethalin + pyroxsulam fenchlorazole B-708 pendimethalin + tembotrione fenchlorazole B-709 pendimethalin + topramezone fenchlorazole B-710 pyroxasulfone + tembotrione fenchlorazole B-711 pyroxasulfone + topramezone fenchlorazole B-712 sulfentrazone + glyphosate fenchlorazole B-713 terbuthylazine + H-1 fenchlorazole B-714 terbuthylazine + foramsulfuron fenchlorazole B-715 terbuthylazine + glyphosate fenchlorazole B-716 terbuthylazine + mesotrione fenchlorazole B-717 terbuthylazine + nicosulfuron fenchlorazole B-718 terbuthylazine + tembotrione fenchlorazole B-719 terbuthylazine + topramezone fenchlorazole B-720 trifluralin + glyphosate fenchlorazole B-721 clodinafop-propargyl isoxadifen B-722 cycloxydim isoxadifen B-723 cyhalofop-butyl isoxadifen B-724 fenoxaprop-P-ethyl isoxadifen B-725 pinoxaden isoxadifen B-726 profoxydim isoxadifen B-727 tepraloxydim isoxadifen B-728 tralkoxydim isoxadifen B-729 esprocarb isoxadifen B-730 prosulfocarb isoxadifen B-731 thiobencarb isoxadifen B-732 triallate isoxadifen B-733 bensulfuron-methyl isoxadifen B-734 bispyribac-sodium isoxadifen B-735 cyclosulfamuron isoxadifen B-736 flumetsulam isoxadifen B-737 flupyrsulfuron-methyl-sodium isoxadifen B-738 foramsulfuron isoxadifen B-739 imazamox isoxadifen B-740 imazapic isoxadifen B-741 imazapyr isoxadifen B-742 imazaquin isoxadifen B-743 imazethapyr isoxadifen B-744 imazosulfuron isoxadifen B-745 iodosulfuron-methyl-sodium isoxadifen B-746 mesosulfuron isoxadifen B-747 nicosulfuron isoxadifen B-748 penoxsulam isoxadifen B-749 propoxycarbazone-sodium isoxadifen B-750 pyrazosulfuron-ethyl isoxadifen B-751 pyroxsulam isoxadifen B-752 rimsulfuron isoxadifen B-753 sulfosulfuron isoxadifen B-754 thiencarbazone-methyl isoxadifen B-755 tritosulfuron isoxadifen B-756 2,4-D and its salts and esters isoxadifen B-757 aminopyralid and its salts and esters isoxadifen B-758 clopyralid and its salts and esters isoxadifen B-759 dicamba and its salts and esters isoxadifen B-760 fluroxypyr-meptyl isoxadifen B-761 quinclorac isoxadifen B-762 quinmerac isoxadifen B-763 H-9 isoxadifen B-764 diflufenzopyr isoxadifen B-765 diflufenzopyr-sodium isoxadifen B-766 clomazone isoxadifen B-767 diflufenican isoxadifen B-768 fluorochloridone isoxadifen B-769 isoxaflutol isoxadifen B-770 mesotrione isoxadifen B-771 picolinafen isoxadifen B-772 sulcotrione isoxadifen B-773 tefuryltrione isoxadifen B-774 tembotrione isoxadifen B-775 topramezone isoxadifen B-776 H-7 isoxadifen B-777 atrazine isoxadifen B-778 diuron isoxadifen B-779 fluometuron isoxadifen B-780 hexazinone isoxadifen B-781 isoproturon isoxadifen B-782 metribuzin isoxadifen B-783 propanil isoxadifen B-784 terbuthylazine isoxadifen B-785 paraquat dichloride isoxadifen B-786 flumioxazin isoxadifen B-787 oxyfluorfen isoxadifen B-788 saflufenacil isoxadifen B-789 sulfentrazone isoxadifen B-790 H-1 isoxadifen B-791 H-2 isoxadifen B-792 glyphosate isoxadifen B-793 glyphosate-isopropylammonium isoxadifen B-794 glyphosate-trimesium (sulfosate) isoxadifen B-795 glufosinate isoxadifen B-796 glufosinate-ammonium isoxadifen B-797 pendimethalin isoxadifen B-798 trifluralin isoxadifen B-799 acetochlor isoxadifen B-800 cafenstrole isoxadifen B-801 dimethenamid-P isoxadifen B-802 fentrazamide isoxadifen B-803 flufenacet isoxadifen B-804 mefenacet isoxadifen B-805 metazachlor isoxadifen B-806 metolachlor-S isoxadifen B-807 pyroxasulfone isoxadifen B-808 isoxaben isoxadifen B-809 dymron isoxadifen B-810 indanofan isoxadifen B-811 oxaziciomefone isoxadifen B-812 triaziflam isoxadifen B-813 atrazine + H-1 isoxadifen B-814 atrazine + glyphosate isoxadifen B-815 atrazine + mesotrione isoxadifen B-816 atrazine + nicosulfuron isoxadifen B-817 atrazine + tembotrione isoxadifen B-818 atrazine + topramezone isoxadifen B-819 clomazone + glyphosate isoxadifen B-820 diflufenican + clodinafop-propargyl isoxadifen B-821 diflufenican + fenoxaprop-P-ethyl isoxadifen B-822 diflufenican + flupyrsulfuron-methyl- isoxadifen sodium B-823 diflufenican + glyphosate isoxadifen B-824 diflufenican + mesosulfuron-methyl isoxadifen B-825 diflufenican + pinoxaden isoxadifen B-826 diflufenican + pyroxsulam isoxadifen B-827 flumetsulam + glyphosate isoxadifen B-828 flumioxazin + glyphosate isoxadifen B-829 imazapic + glyphosate isoxadifen B-830 imazethapyr + glyphosate isoxadifen B-831 isoxaflutol + H-1 isoxadifen B-832 isoxaflutol + glyphosate isoxadifen B-833 metazachior + H-1 isoxadifen B-834 metazachlor + glyphosate isoxadifen B-835 metazachlor + mesotrione isoxadifen B-836 metazachlor + nicosulfuron isoxadifen B-837 metazachlor + terbuthylazine isoxadifen B-838 metazachlor + topramezone isoxadifen B-839 metribuzin + glyphosate isoxadifen B-840 pendimethalin + H-1 isoxadifen B-841 pendimethalin + clodinafop-propargyl isoxadifen B-842 pendimethalin + fenoxaprop-P-ethyl isoxadifen B-843 pendimethalin + flupyrsulfuron-methyl- isoxadifen sodium B-844 pendimethalin + glyphosate isoxadifen B-845 pendimethalin + mesosulfuron-methyl isoxadifen B-846 pendimethalin + mesotrione isoxadifen B-847 pendimethalin + nicosulfuron isoxadifen B-848 pendimethalin + pinoxaden isoxadifen B-849 pendimethalin + pyroxsulam isoxadifen B-850 pendimethalin + tembotrione isoxadifen B-851 pendimethalin + topramezone isoxadifen B-852 pyroxasulfone + tembotrione isoxadifen B-853 pyroxasulfone + topramezone isoxadifen B-854 sulfentrazone + glyphosate isoxadifen B-855 terbuthylazine + H-1 isoxadifen B-856 terbuthylazine + foramsulfuron isoxadifen B-857 terbuthylazine + glyphosate isoxadifen B-858 terbuthylazine + mesotrione isoxadifen B-859 terbuthylazine + nicosulfuron isoxadifen B-860 terbuthylazine + tembotrione isoxadifen B-861 terbuthylazine + topramezone isoxadifen B-862 trifluralin + glyphosate isoxadifen B-863 clodinafop-propargyl mefenpyr B-864 cycloxydim mefenpyr B-865 cyhalofop-butyl mefenpyr B-866 fenoxaprop-P-ethyl mefenpyr B-867 pinoxaden mefenpyr B-868 profoxydim mefenpyr B-869 tepraloxydim mefenpyr B-870 tralkoxydim mefenpyr B-871 esprocarb mefenpyr B-872 prosulfocarb mefenpyr B-873 thiobencarb mefenpyr B-874 triallate mefenpyr B-875 bensulfuron-methyl mefenpyr B-876 bispyribac-sodium mefenpyr B-877 cyclosulfamuron mefenpyr B-878 flumetsulam mefenpyr B-879 flupyrsulfuron-methyl-sodium mefenpyr B-880 foramsulfuron mefenpyr B-881 imazamox mefenpyr B-882 imazapic mefenpyr B-883 imazapyr mefenpyr B-884 imazaquin mefenpyr B-885 imazethapyr mefenpyr B-886 imazosulfuron mefenpyr B-887 iodosulfuron-methyl-sodium mefenpyr B-888 mesosulfuron mefenpyr B-889 nicosulfuron mefenpyr B-890 penoxsulam mefenpyr B-891 propoxycarbazone-sodium mefenpyr B-892 pyrazosulfuron-ethyl mefenpyr B-893 pyroxsulam mefenpyr B-894 rimsulfuron mefenpyr B-895 sulfosulfuron mefenpyr B-896 thiencarbazone-methyl mefenpyr B-897 tritosulfuron mefenpyr B-898 2,4-D and its salts and esters mefenpyr B-899 aminopyralid and its salts and esters mefenpyr B-900 clopyralid and its salts and esters mefenpyr B-901 dicamba and its salts and esters mefenpyr B-902 fluroxypyr-meptyl mefenpyr B-903 quinclorac mefenpyr B-904 quinmerac mefenpyr B-905 H-9 mefenpyr B-906 diflufenzopyr mefenpyr B-907 diflufenzopyr-sodium mefenpyr B-908 clomazone mefenpyr B-909 diflufenican mefenpyr B-910 fluorochloridone mefenpyr B-911 isoxaflutol mefenpyr B-912 mesotrione mefenpyr B-913 picolinafen mefenpyr B-914 sulcotrione mefenpyr B-915 tefuryltrione mefenpyr B-916 tembotrione mefenpyr B-917 topramezone mefenpyr B-918 H-7 mefenpyr B-919 atrazine mefenpyr B-920 diuron mefenpyr B-921 fluometuron mefenpyr B-922 hexazinone mefenpyr B-923 isoproturon mefenpyr B-924 metribuzin mefenpyr B-925 propanil mefenpyr B-926 terbuthylazine mefenpyr B-927 paraquat dichloride mefenpyr B-928 flumioxazin mefenpyr B-929 oxyfluorfen mefenpyr B-930 saflufenacil mefenpyr B-931 sulfentrazone mefenpyr B-932 H-1 mefenpyr B-933 H-2 mefenpyr B-934 glyphosate mefenpyr B-935 glyphosate-isopropylammonium mefenpyr B-936 glyphosate-trimesium (sulfosate) mefenpyr B-937 glufosinate mefenpyr B-938 glufosinate-ammonium mefenpyr B-939 pendimethalin mefenpyr B-940 trifluralin mefenpyr B-941 acetochlor mefenpyr B-942 cafenstrole mefenpyr B-943 dimethenamid-P mefenpyr B-944 fentrazamide mefenpyr B-945 flufenacet mefenpyr B-946 mefenacet mefenpyr B-947 metazachlor mefenpyr B-948 metolachlor-S mefenpyr B-949 pyroxasulfone mefenpyr B-950 isoxaben mefenpyr B-951 dymron mefenpyr B-952 indanofan mefenpyr B-953 oxaziclomefone mefenpyr B-954 triaziflam mefenpyr B-955 atrazine + H-1 mefenpyr B-956 atrazine + glyphosate mefenpyr B-957 atrazine + mesotrione mefenpyr B-958 atrazine + nicosulfuron mefenpyr B-959 atrazine + tembotrione mefenpyr B-960 atrazine + topramezone mefenpyr B-961 clomazone + glyphosate mefenpyr B-962 diflufenican + clodinafop-propargyl mefenpyr B-963 diflufenican + fenoxaprop-P-ethyl mefenpyr B-964 diflufenican + flupyrsulfuron-methyl- mefenpyr sodium B-965 diflufenican + glyphosate mefenpyr B-966 diflufenican + mesosulfuron-methyl mefenpyr B-967 diflufenican + pinoxaden mefenpyr B-968 diflufenican + pyroxsulam mefenpyr B-969 flumetsulam + glyphosate mefenpyr B-970 flumioxazin + glyphosate mefenpyr B-971 imazapic + glyphosate mefenpyr B-972 imazethapyr + glyphosate mefenpyr B-973 isoxaflutol + H-1 mefenpyr B-974 isoxaflutol + glyphosate mefenpyr B-975 metazachlor + H-1 mefenpyr B-976 metazachlor + glyphosate mefenpyr B-977 metazachlor + mesotrione mefenpyr B-978 metazachlor + nicosulfuron mefenpyr B-979 metazachlor + terbuthylazine mefenpyr B-980 metazachlor + topramezone mefenpyr B-981 metribuzin + glyphosate mefenpyr B-982 pendimethalin + H-1 mefenpyr B-983 pendimethalin + clodinafop-propargyl mefenpyr B-984 pendimethalin + fenoxaprop-P-ethyl mefenpyr B-985 pendimethalin + flupyrsulfuron-methyl- mefenpyr sodium B-986 pendimethalin + glyphosate mefenpyr B-987 pendimethalin + mesosulfuron-methyl mefenpyr B-988 pendimethalin + mesotrione mefenpyr B-989 pendimethalin + nicosulfuron mefenpyr B-990 pendimethalin + pinoxaden mefenpyr B-991 pendimethalin + pyroxsulam mefenpyr B-992 pendimethalin + tembotrione mefenpyr B-993 pendimethalin + topramezone mefenpyr B-994 pyroxasulfone + tembotrione mefenpyr B-995 pyroxasulfone + topramezone mefenpyr B-996 sulfentrazone + glyphosate mefenpyr B-997 terbuthylazine + H-1 mefenpyr B-998 terbuthylazine + foramsulfuron mefenpyr B-999 terbuthylazine + glyphosate mefenpyr B-1000 terbuthylazine + mesotrione mefenpyr B-1001 terbuthylazine + nicosulfuron mefenpyr B-1002 terbuthylazine + tembotrione mefenpyr B-1003 terbuthylazine + topramezone mefenpyr B-1004 trifluralin + glyphosate mefenpyr B-1005 clodinafop-propargyl H-12 B-1006 cycloxydim H-12 B-1007 cyhalofop-butyl H-12 B-1008 fenoxaprop-P-ethyl H-12 B-1009 pinoxaden H-12 B-1010 profoxydim H-12 B-1011 tepraloxydim H-12 B-1012 tralkoxydim H-12 B-1013 esprocarb H-12 B-1014 prosulfocarb H-12 B-1015 thiobencarb H-12 B-1016 triallate H-12 B-1017 bensulfuron-methyl H-12 B-1018 bispyribac-sodium H-12 B-1019 cyclosulfamuron H-12 B-1020 flumetsulam H-12 B-1021 flupyrsulfuron-methyl-sodium H-12 B-1022 foramsulfuron H-12 B-1023 imazamox H-12 B-1024 imazapic H-12 B-1025 imazapyr H-12 B-1026 imazaquin H-12 B-1027 imazethapyr H-12 B-1028 imazosulfuron H-12 B-1029 iodosulfuron-methyl-sodium H-12 B-1030 mesosulfuron H-12 B-1031 nicosulfuron H-12 B-1032 penoxsulam H-12 B-1033 propoxycarbazone-sodium H-12 B-1034 pyrazosulfuron-ethyl H-12 B-1035 pyroxsulam H-12 B-1036 rimsulfuron H-12 B-1037 sulfosulfuron H-12 B-1038 thiencarbazone-methyl H-12 B-1039 tritosulfuron H-12 B-1040 2,4-D and its salts and esters H-12 B-1041 aminopyralid and its salts and esters H-12 B-1042 clopyralid and its salts and esters H-12 B-1043 dicamba and its salts and esters H-12 B-1044 fluroxypyr-meptyl H-12 B-1045 quinclorac H-12 B-1046 quinmerac H-12 B-1047 B-9 H-12 B-1048 diflufenzopyr H-12 B-1049 diflufenzopyr-sodium H-12 B-1050 clomazone H-12 B-1051 diflufenican H-12 B-1052 fluorochloridone H-12 B-1053 isoxaflutol H-12 B-1054 mesotrione H-12 B-1055 picolinafen H-12 B-1056 sulcotrione H-12 B-1057 tefuryltrione H-12 B-1058 tembotrione H-12 B-1059 topramezone H-12 B-1060 H-7 H-12 B-1061 atrazine H-12 B-1062 diuron H-12 B-1063 fluometuron H-12 B-1064 hexazinone H-12 B-1065 isoproturon H-12 B-1066 metribuzin H-12 B-1067 propanil H-12 B-1068 terbuthylazine H-12 B-1069 paraquat dichloride H-12 B-1070 flumioxazin H-12 B-1071 oxyfluorfen H-12 B-1072 saflufenacil H-12 B-1073 sulfentrazone H-12 B-1074 H-1 H-12 B-1075 H-2 H-12 B-1076 glyphosate H-12 B-1077 glyphosate-isopropylammonium H-12 B-1078 glyphosate-trimesium (sulfosate) H-12 B-1079 glufosinate H-12 B-1080 glufosinate-ammonium H-12 B-1081 pendimethalin H-12 B-1082 trifluralin H-12 B-1083 acetochlor H-12 B-1084 cafenstrole H-12 B-1085 dimethenamid-P H-12 B-1086 fentrazamide H-12 B-1087 flufenacet H-12 B-1088 mefenacet H-12 B-1089 metazachlor H-12 B-1090 metolachlor-S H-12 B-1091 pyroxasulfone H-12 B-1092 isoxaben H-12 B-1093 dymron H-12 B-1094 indanofan H-12 B-1095 oxaziclomefone H-12 B-1096 triaziflam H-12 B-1097 atrazine + H-1 H-12 B-1098 atrazine + glyphosate H-12 B-1099 atrazine + mesotrione H-12 B-1100 atrazine + nicosulfuron H-12 B-1101 atrazine + tembotrione H-12 B-1102 atrazine + topramezone H-12 B-1103 clomazone + glyphosate H-12 B-1104 diflufenican + clodinafop-propargyl H-12 B-1105 diflufenican + fenoxaprop-P-ethyl H-12 B-1106 diflufenican + flupyrsulfuron-methyl- H-12 sodium B-1107 diflufenican + glyphosate H-12 B-1108 diflufenican + mesosulfuron-methyl H-12 B-1109 diflufenican + pinoxaden H-12 B-1110 diflufenican + pyroxsulam H-12 B-1111 flumetsulam + glyphosate H-12 B-1112 flumioxazin + glyphosate H-12 B-1113 imazapic + glyphosate H-12 B-1114 imazethapyr + glyphosate H-12 B-1115 isoxaflutol + H-1 H-12 B-1116 isoxaflutol + glyphosate H-12 B-1117 metazachlor + H-1 H-12 B-1118 metazachlor + glyphosate H-12 B-1119 metazachlor + mesotrione H-12 B-1120 metazachlor + nicosulfuron H-12 B-1121 metazachlor + terbuthylazine H-12 B-1122 metazachlor + topramezone H-12 B-1123 metribuzin + glyphosate H-12 B-1124 pendimethalin + H-1 H-12 B-1125 pendimethalin + clodinafop-propargyl H-12 B-1126 pendimethalin + fenoxaprop-P-ethyl H-12 B-1127 pendimethalin + flupyrsulfuron-methyl- H-12 sodium B-1128 pendimethalin + glyphosate H-12 B-1129 pendimethalin + mesosulfuron-methyl H-12 B-1130 pendimethalin + mesotrione H-12 B-1131 pendimethalin + nicosulfuron H-12 B-1132 pendimethalin + pinoxaden H-12 B-1133 pendimethalin + pyroxsulam H-12 B-1134 pendimethalin + tembotrione H-12 B-1135 pendimethalin + topramezone H-12 B-1136 pyroxasulfone + tembotrione H-12 B-1137 pyroxasulfone + topramezone H-12 B-1138 sulfentrazone + glyphosate H-12 B-1139 terbuthylazine + H-1 H-12 B-1140 terbuthylazine + foramsulfuron H-12 B-1141 terbuthylazine + glyphosate H-12 B-1142 terbuthylazine + mesotrione H-12 B-1143 terbuthylazine + nicosulfuron H-12 B-1144 terbuthylazine + tembotrione H-12 B-1145 terbuthylazine + topramezone H-12 B-1146 trifluralin + glyphosate H-12 B-1147 2-1 — B-1148 2-2 — B-1149 2-3 — B-1150 2-4 — B-1151 2-5 — B-1152 2-6 — B-1153 2-7 — B-1154 2-8 — B-1155 2-9 — B-1156 2-1 benoxacor B-1157 2-2 benoxacor B-1158 2-3 benoxacor B-1159 2-4 benoxacor B-1160 2-5 benoxacor B-1161 2-6 benoxacor B-1162 2-7 benoxacor B-1163 2-8 benoxacor B-1164 2-9 benoxacor B-1165 2-1 cloquintocet B-1166 2-2 cloquintocet B-1167 2-3 cloquintocet B-1168 2-4 cloquintocet B-1169 2-5 cloquintocet B-1170 2-6 cloquintocet B-1171 2-7 cloquintocet B-1172 2-8 cloquintocet B-1173 2-9 cloquintocet B-1174 2-1 cyprosulfamide B-1175 2-2 cyprosulfamide B-1176 2-3 cyprosulfamide B-1177 2-4 cyprosulfamide B-1178 2-5 cyprosulfamide B-1179 2-6 cyprosulfamide B-1180 2-7 cyprosulfamide B-1181 2-8 cyprosulfamide B-1182 2-9 cyprosulfamide B-1183 2-1 dichlormid B-1184 2-2 dichlormid B-1185 2-3 dichlormid B-1186 2-4 dichlormid B-1187 2-5 dichlormid B-1188 2-6 dichlormid B-1189 2-7 dichlormid B-1190 2-8 dichlormid B-1191 2-9 dichlormid B-1192 2-1 fenchlorazole B-1193 2-2 fenchlorazole B-1194 2-3 fenchlorazole B-1195 2-4 fenchlorazole B-1196 2-5 fenchlorazole B-1197 2-6 fenchlorazole B-1198 2-7 fenchlorazole B-1199 2-8 fenchlorazole B-1200 2-9 fenchlorazole B-1201 2-1 isoxadifen B-1202 2-2 isoxadifen B-1203 2-3 isoxadifen B-1204 2-4 isoxadifen B-1205 2-5 isoxadifen B-1206 2-6 isoxadifen B-1207 2-7 isoxadifen B-1208 2-8 isoxadifen B-1209 2-9 isoxadifen B-1210 2-1 mefenpyr B-1211 2-2 mefenpyr B-1212 2-3 mefenpyr B-1213 2-4 mefenpyr B-1214 2-5 mefenpyr B-1215 2-6 mefenpyr B-1216 2-7 mefenpyr B-1217 2-8 mefenpyr B-1218 2-9 mefenpyr B-1219 2-1 H-11 B-1220 2-2 H-11 B-1221 2-3 H-11 B-1222 2-4 H-11 B-1223 2-5 H-11 B-1224 2-6 H-11 B-1225 2-7 H-11 B-1226 2-8 H-11 B-1227 2-9 H-11 B-1228 2-1 H-12 B-1229 2-2 H-12 B-1230 2-3 H-12 B-1231 2-4 H-12 B-1232 2-5 H-12 B-1233 2-6 H-12 B-1234 2-7 H-12 B-1235 2-8 H-12 B-1236 2-9 H-12

The compounds of formula I and the compositions according to the invention may also have a plant-strengthening action. Accordingly, they are suitable for mobilizing the defense system of the plants against attack by unwanted microorganisms, such as harmful fungi, but also viruses and bacteria. Plant-strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances which are capable of stimulating the defense system of treated plants in such a way that, when subsequently inoculated by unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms.

The compounds of formula I can be employed for protecting plants against attack by unwanted microorganisms within a certain period of time after the treatment. The period of time within which their protection is effected generally extends from 1 to 28 days, preferably from 1 to 14 days, after the treatment of the plants with the compounds of formula I, or, after treatment of the seed, for up to 9 months after sowing.

The compounds of formula I and the compositions according to the invention are also suitable for increasing the harvest yield.

Moreover, they have reduced toxicity and are tolerated well by the plants.

The following examples will further illustrate the invention:

With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds I. The compounds obtained in this manner are listed in the tables that follow, together with physical data. The products shown below were characterized by determination of the melting point, NMR spectroscopy or the masses ([m/z]) determined by HPLC-MS spectrometry.

HPLC-MS=high performance liquid chromatography coupled with mass spectrometry;

HPLC column: RP-18 column (Chromolith Speed ROD from Merck KgaA, Germany), 50*4.6 mm; mobile phase: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% TFA, using a gradient from 5:95 to 100:0 over 5 minutes at 40° C., flow rate 1.8 mI/min.

MS: quadrupole electrospray ionization, 80 V (positive mode).

HPLC column: Luna-C₁₈(2) 5 μm column (Phenomenex), 2.0*50 mm; mobile phase: acetonitrile+0.0625% trifluoroacetic acid (TFA)/water+0.0675% TFA, using a gradient from 10:90 to 80:20 over 4.0 minutes at 40° C., flow rate 0.8 ml/min.

MS: quadrupole electrospray ionization, 70 V (positive mode).

EtOAc: acetic acid ethyl ester

THF: tetrahydrofuran

LiHMDS: lithium bis(trimethylsilyl)amide

m-CPBA: 3-chloroperoxybenzoic acid

TFA: trifluoroacetic acid

WORKING EXAMPLE Synthesis of 4-methyl-1,2,4-triazol-3-amine

A solution of 1-aminoguanidine-hydrochloride (50 g, 0.45 mol) and MeNCS (280 g, 3.8 mol) in EtOH (500 ml) was stirred in an autoclave at 150° C. for 4 hours. After this time, it was cooled to 25° C., concentrated, re-dissolved in water (700 mL) and K₂CO₃ (62.5 g, 0.55 mol) was added. The reaction mixture was stirred under reflux for 16 hours and the reaction was cooled to 25° C. The solvent was removed under vacuum to give the crude, which was dissolved in MeOH and filtered. The filtrate was concentrated. The residue was purified by column chromatography on silica gel column eluted with DCM: MeOH (30:1 to 10:1 to 5:1) to give the 3-amino-4-methyl-1H-1,2,4-triazole-5-thione (20 g, 31%) as a white solid.

To a solution of 3-amino-4-methyl-1H-1,2,4-triazole-5-thione (25 g, 0.2 mol) in DCM (300 mL) was added a solution of H₂O₂(86 g, 0.6 mol, 30%) in CH₃COOH (150 mL) at 0-5° C. The reaction mixture was stirred at 25° C. for 4 hours. The reaction mixture was quenched by adding a saturated aqueous solution of Na₂SO₃ and a aqueous solution of NaOH until pH 10. The aqueous layer was separated and concentrated under vacuum to give the crude product. The product was dissolved in a DCM: MeOH=10:1 (30 mL) mixture and the remaining solid was discarded. The solvent was removed to give 4-methyl-1,2,4-triazol-3-amine (5 g, 23%) as a white solid.

¹H NMR (MeOD, 400 MHz): δ 3.47 (s, 3H) 7.91 (s, 1H).

Following the same procedure, 4-ethyl-1,2,4-triazol-3-amine was also obtained

¹H NMR (MeOD, 400 MHz): δ 1.36 (t, J=7.2 Hz, 3H) 3.87 (q, J=7.2 Hz, 2H) 7.98 (s, 1H).

Synthesis of 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoylchloride

2,6-dichloro-4-fluoro-aniline (12 g, 67 mmol) was taken up in concentrated HCl (13 mL) and water (51 mL) at 0° C. After stirring for 15 min, a solution of NaNO₂ (4.85 g, 70.3 mmol) in water (10 mL) was added drop-wise at 0° C. and the mixture was stirred for 45 min. A solution of MeSNa (35 g, 100 mmol) and Na₂CO₃ (10.6 g, 100 mmol) in water (100 mL) was then added to the above solution drop-wise at 50° C. After addition, the mixture was stirred for 1 hour, then extracted with EtOAc and the combined organic layers were dried (MgSO₄), filtered and the filtrate concentrated in vacuo to give the crude product. Flash chromatography using neat 60-90 petrol ether afforded 1,3-dichloro-5-fluoro-2-methylsulfanyl-benzene (4.7 g, 34%).

¹H NMR (CDCl₃, 400 MHz): δ7.17 (d, 2H), 2.41 (s, 3H).

To a solution of 1,3-dichloro-5-fluoro-2-methylsulfanyl-benzene (4.7 g, 22.5 mmol) in anhydrous THF (100 mL) was added ^(t)BuLi.THF (15 mL, 44.5 mmol, 3.0 M) drop-wise at −78° C. under a nitrogen atmosphere. After stirring for 50 min, dry ice was added and the mixture was allowed to warm to ambient temperature. The reaction was quenched by addition of sat. aqueous NH₄Cl and extracted with EtOAc. The combined organic layers were dried (MgSO₄), filtered and the filtrate concentrated in vacuo to afford 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoic acid (3.6 g, 63%).

¹H NMR (CDCl₃, 400 MHz): δ 7.30 (d, 1H), 2.44 (s, 3H).

A mixture of 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoic acid (750 mg, 2.95 mmol) and (COCl)₂ (1.13 g, 8.86 mmol) in CH₂Cl₂ (10 mL) was stirred for 2 hours at 0° C. The solvent was evaporated under reduced pressure to afford 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoylchloride used as the crude product (750 mg).

Synthesis of 2,4-dichloro-3-ethoxy-6-fluoro-benzoyl chloride

To a solution of 2,6-dichloro-4-fluoro-phenol (2 g, 11.11 mmol) in 20 mL anhydrous DMF was added K₂CO₃ (3.07 g, 22.22 mmol) at room temperature. After stirring for 30 min, Etl (3.47 g, 22.22 mmol) was added and the mixture was stirred at room temperature overnight. Water was added and the product was extracted with MTBE. The organic phase was washed with brine, dried and concentrated in vacuum to give the crude product, which was purified by column chromatography eluted with 100% cyclohexane to afford 1,3-dichloro-2-ethoxy-5-fluorobenzene (1.5 g, 64.9%).

¹H NMR (CDCl3, 400 MHz): δ 1.46 (t, J=7.03 Hz, 3H) 4.07 (q, J7.03 Hz, 2H) 7.07 (d, J=7.78 Hz, 2H).

To a solution of diisopropylamine (1.5 mL, 10.5 mmol) in 10 mL anhydrous THF was added n-BuLi (3.5 mL, 8.75 mmol) dropwise at 0° C. under nitrogen and the mixture was stirred 30 min at 0° C. To 1,3-dichloro-2-ethoxy-5-fluoro-benzene (1.5 g, 7.21 mmol) in 30 mL anhydrous THF was added, dropwise, the freshly prepared LDA solution at −78° C. under nitrogen and the mixture was stirred for 1.5 hours. Then dry ice was added and the reaction was let to warm to room temperature. The reaction was quenched with sat. NH₄Cl solution and THF was evaporated. Water was added to the residue and it was basified with a saturated NaHCO₃ solution, extracted twice with DCM. Then the aqueous layer was acidified with 3N HCl to pH 1 and extracted with EtOAc. The organic phase was washed with brine, dried and concentrated in vacuum to give 2,4-dichloro-3-ethoxy-6-fluoro-benzoic acid (1 g, 55.0%).

1H NMR (CDCl₃, 400 MHz): δ 1.49 (t, J=7.03 Hz, 3H) 4.10 (q, J=7.03 Hz, 2H) 7.20 (d, J=8.53 Hz, 1H).

To a solution of 2,4-dichloro-3-ethoxy-6-fluoro-benzoic acid (300 mg, 1.19 mmol) in 15 mL anhydrous DCM was added (COCl)₂ (0.17 mL, 1.79 mmol) and 1 drop of DMF at 0° C. The mixture was stirred at room temperature for 2 hrs. The solution was concentrated in vacuum to afford 2,4-dichloro-3-ethoxy-6-fluoro-benzoyl chloride used directly in the next step (300 mg)

Example 1 Preparation of 2,4-dichloro-6-fluoro-3-methylsulfanyl-N-(4-methyl-1,2,4-triazol-3-yl)benzamide (cpd. 4)

To a solution of 4-methyl-1,2,4-triazol-3-amine (100 mg, 1.02 mmol) in 50 mL anhydrous THF was added n-BuLi (1.5 mL, 3.06 mmol) at −78° C. under nitrogen. After stirring for 30 min, 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoylchloride (200 mg, 1.02 mmol) in 5 mL THF was added and the mixture was stirred for 2 hours at this temperature and was let to warm to room temperature. The reaction was quenched by adding a NH₄Cl solution (20 mL), extracted with EtOAc (20 mL*3). The combined organic layers were combined, dried over Na₂SO₄, filtered and concentrated to give the crude product which was purified by prep-HPLC (25 mg, 8.36%, M+1=336).

¹H NMR (MeOD, 400 MHz): δ 2.41 (s, 3H) 3.71 (s, 3H) 7.55 (d, J=9.2 Hz, 1H) 8.53 (s, 1H).

Example 2 Preparation of 2,4-dichloro-6-fluoro-3-methylsulfonyl-N-(4-methyl-1,2,4-triazol-3-yl)benzamide (cpd. 5)

To a solution of 2,4-dichloro-6-fluoro-3-methylsulfanyl-N-(4-methyl-1,2,4-triazol-3-yl)benzamide (170 mg, 0.49 mmol) in 5 mL anhydrous DCM was added m-CPBA (260 mg, 1.47 mmol) at 0° C. The mixture was stirred for 2 days at room temperature. Then the organic layer was quenched by a adding a saturated Na₂SO₃ solution. The organic layer was washed with a sat. NaHCO₃ solution twice, dried over Na₂SO₄ and concentrated to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-6-fluoro-3-methylsulfonyl-N-(4-methyl-1,2,4-triazol-3-yl)benzamide (128 mg, 48.5%, M+1=367).

¹H NMR: (MeOD, 400 MHz): δ 3.39 (s, 3H) 3.64 (s, 3H) 7.67 (d, J=8.0 Hz, 1H) 8.43 (s, 1H).

Example 3 Preparation of 2,4-dichloro-N-(4-ethyl-1,2,4-triazol-3-yl)-6-fluoro-3 methyl-sulfanyl-benzamide (cpd. 3)

To a solution of 4-ethyl-1,2,4-triazol-3-amine (350 mg, 3.12 mmol) in 50 mL anhydrous THF was added LiHMDS (15 mL, 12.4 mmol) at −78° C. under nitrogen. After stirring for 15 min, 2,4-dichloro-6-fluoro-3-methylsulfanyl-benzoylchloride (843 mg, 3.57 mmol) in 5 mL THF was added and the mixture was stirred for 2 hours at this temperature and let to warm to room temperature. The reaction was quenched by adding a saturated NH₄Cl solution (50 mL), extracted with EtOAc (50 mL*3). The combined organic layers were combined, dried over Na₂SO₄, filtered and concentrated to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-N-(4-ethyl-1,2,4-triazol-3-yl)-6-fluoro-3 methyl-sulfanyl-benzamide (90 mg, 8.36%, M+1=349).

¹H NMR (MeOD 400 MHz): δ 1.43 (t, J=7.6 Hz, 3H) 2.41 (s, 3H) 4.06 (q, J=7.2 Hz, 2H) 7.50 (d, J=8.8 Hz, 1H) 8.47 (s,1H).

Example 4 Preparation of 2,4-dichloro-N-(4-ethyl-1,2,4-triazol-3-yl)-6-fluoro-3-methyl-sulfonyl-benzamide (cpd. 2)

To a solution of 2,4-dichloro-N-(4-ethyl-1,2,4-triazol-3-yl)-6-fluoro-3 methyl-sulfanyl-benzamide (170 mg, 0.49 mmol) in 5 mL anhydrous DCM was added m-CPBA (260 mg, 1.47 mmol) at 0° C. The mixture was stirred for 2 days at room temperature. Then the reaction was quenched by adding a saturated Na₂SO₃ solution. The organic layer was washed with a sat. NaHCO₃ solution twice, dried over Na₂SO₄ and concentrated to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-N-(4-ethyl-1,2,4-triazol-3-yl)-6-fluoro-3-methyl-sulfonyl-benzamide (90 mg, 47.5%, M+1=381).

¹H NMR (MeOD 400 MHz): δ 1.44 (t, J=7.2 Hz, 3H) 3.89 (s, 3H) 4.08-4.09 (m, 2H) 7.66 (s, 1H) 8.56 (s, 1H).

Example 5 Preparation of 2,4-dichloro-3-ethoxy-N-(4-ethyl-1,2,4-triazol-3-yl)-6-fluorobenzamide (cpd. 7)

To a solution of 4-ethyl-1,2,4-triazol-3-amine (134 mg, 1.20 mmol) in 60 mL anhydrous THF was added LiHMDS (3.6 mL, 3.6 mmol) at −78° C. under nitrogen and the mixture was allowed to warm to −40° C. After stirred for 3 hours, the mixture was cooled to −78° C. and was added to a solution of 2,4-dichloro-3-ethoxy-6-fluoro-benzoyl chloride in 15 mL THF. The mixture was stirred at room temperature overnight. The reaction was quenched by adding a NH₄Cl solution (150 mL), extracted with EtOAc. The organic phase was washed with brine, dried and concentrated in vacuum to give the crude product, which was purified by prep-HPLC to afford 2,4-dichloro-3-ethoxy-N-(4-ethyl-1,2,4-triazol-3-yl)-6-fluoro-benzamide (220 mg, 53.0%, M+1=347).

¹H NMR: (MeOD 400 MHz): δ 1.45 (t, J=7.03 Hz, 6H) 3.88-4.30 (m, 4H) 7.42 (d, J=8.53 Hz, 1H) 8.53 (s, 1H).

By analogy to the methods described in the Examples above, the following compounds of formula I according to Table 211 were prepared:

TABLE 211

in tables cpd. no 1 to 210 R¹ R² R³ R⁴ R⁵ R⁶ R⁷ MS (m/z) 2 I.B5-2.94 Cl SO₂CH₃ Cl H F H CH₂CH₃ 381.0 3 I.B3-2.94 Cl SCH₃ Cl H F H CH₂CH₃ 348.9 4 I.B3-2.93 Cl SCH₃ Cl H F H CH₃ 334.9 5 I.B5-2.93 Cl SO₂CH₃ Cl H F H CH₃ 366.9 6 — Cl OCH₂CH₂OCH₃ Cl H F H CH₂CH₃ 377.1 7 — Cl OCH₂CH₃ Cl H F H CH₂CH₃ 346.9 8 — Cl OCH₂CF₃ Cl H F H CH₂CH₃ 401.0

Use Examples

The herbicidal activity of the compunds of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this has been impaired by the active ingredients.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of at least 70 and a very good herbicidal activity is given at values of at least 85.

The plants used in the greenhouse experiments belonged to the following species:

Bayer Code Scientific name English name I ABUTH Abutilon theophrasti velvetleaf II ALOMY Alopecurus agrestis black-grass III AMARE Amaranthus retroflexus common amaranth IV APESV Agrostis spica-venti loose silky bent V AVEFA Avena fatua coomon wild oat VI ECHCG Echinochloa crus-galli common barnyardgrass VII SETFA Setaria faberi giant foxtail VIII SETVI Setaria viridis green foxtail Following representative compounds of formula I according to Table 211 were used in post-emergence treatments in greenhouse experiments (values labeled with * result from pre-emergence experiments):

TABLE 212 treatment damage [%] in weed species cpd. no. [g/ha] I II III IV V VI VII VIII 1 2 1000 100 — 75, 95* 80* 75 90, 98* 85* 100 2 3 1000 100, 90* — 100, 90*  — 80 98, 75* 70* 100 3 4 1000 100, 70* 90 100, 100* 70* 90 95 70* 100 4 5 1000  98, 80* 85 90, 85* 70* — 98, 80* 85* 95 

1-19. (canceled)
 20. A compound of formula I,

wherein R¹ is selected from the group consisting of cyano-Z¹, halogen, nitro, C₁-C₈-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₁₀-cycloalkyl-Z¹, C₁-C₈-haloalkyl, C₂-C₈-haloalkenyl, C₃-C₈-haloalkynyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹, Rlb-S(O)_(k)—Z¹, phenoxy-Z¹, and heterocyclyloxy-Z¹, wherein heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, wherein the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R¹¹, which are identical or different; X is N or CR²; R², R³ are identical or different and independently selected from the group consisting of hydrogen, halogen, OH—Z², NO₂—Z², cyano-Z², C₁-C₆-alkyl, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₃-C₁₀-cycloalkyl-Z², C₃-C₁₀-cycloalkoxy-Z², wherein the C₃-C₁₀-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₈-haloalkyl, C₂-C₈-haloalkenyl, C₃-C₈-haloalkynyl, C₁-C₈-alkoxy-Z², C₁-C₈-haloalkoxy-Z², C₃-C₁₀-cycloalkyl-C₁-C₂-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z², C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z², C₂-C₈-alkenyloxy-Z², C₂-C₈-alkynyloxy-Z², C₂-C₈-haloalkenyloxy-Z², C₃-C₈-haloalkynyloxy-Z², C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z², (tri-C₁-C₄-alkyl)silyl-Z², R^(2b)—S(O)_(k)—Z², R^(2c)—C(═O)—Z², R^(2d)O—C(═O)—Z, R^(2d)O—N═CH—Z², R^(2c)R^(2d)C═N—O—C₁-C₄-alkyl, R²eR^(2f)N—C(═O)—Z², R^(2g)R^(2h)N—Z², phenyl-Z²-a and heterocyclyl-Z^(2a), wherein heterocyclyl is a 3-, 4-, 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, wherein the cyclic groups in phenyl-Z^(2a) and heterocyclyl-Z^(2a) are unsubstituted or substituted by 1, 2, 3 or 4 groups R²¹, which are identical or different; or R² and R³ together form a saturated 5- or 6-membered ring, optionally containing an oxygen or a S(O)_(n) heteroatom, the 5- or 6-membered ring being unsubstituted or substituted by 1, 2 or 3 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl and C₁-C₄-alkoxy; R⁴ is selected from the group consisting of hydrogen, cyano-Z¹, halogen, nitro, C₁-C₈-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino, C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k), C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹, R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, wherein heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, wherein the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R¹¹, which are identical or different; R⁵ is selected from the group consisting of cyano-Z¹, halogen, nitro, C₁-C₈-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-haloalkyl, C₁-C₃-alkylamino, C₁-C₃-dialkylamino, C₁-C₃-alkylamino-S(O)_(k), C₁-C₃-alkylcarbonyl, C₁-C₈-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-Z¹, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkylthio-Z¹, C₂-C₆-alkenyloxy, C₂-C₆-alkynyloxy, C₁-C₆-haloalkoxy, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkoxy-Z¹, R^(1b)—S(O)_(k)—Z¹, phenoxy-Z¹ and heterocyclyloxy-Z¹, wherein heterocyclyloxy is an oxygen bound 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, wherein the cyclic groups in phenoxy and heterocyclyloxy are unsubstituted or substituted by 1, 2, 3 or 4 groups R¹¹, which are identical or different; R⁶ is selected from the group consisting of hydrogen, CN, nitro, hydroxy, amino, C₁-C₆-alkyl, C₁-C₆-cyano-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylcarbonyl, C₁-C₆-alkyaminocarbonyl, C₁-C₆-dialkyl-aminocarbonyl, C₁-C₆-alkyamino, C₁-C₆-dialkyl-amino, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, R^(b)R^(b)N—S(O)_(n)—Z, R^(b)O—S(O)_(n)—Z, R^(b)—S(O)_(n)—Z, R^(c)R^(c)N—C₁-C₃-alkyl-S(O)—C₁-C₃-alkyl, R^(c)—C(═O)—C₁-C₃-alkyl, R^(d)—C(═O)O—C₁-C₃-alkyl, R^(d)—O—C(═O)O—C₁-C₃-alkyl, R^(d)O—C(═O)—C₁-C₃-alkyl, R^(e)R^(f)N—C(═O)—C₁-C₃-alkyl, R^(c)—C(═O)R^(e)N—C₁-C₃-alkyl, R^(b)—S(O)_(n)—R^(e)N—C₁-C₃-alkyl, R^(c)R^(c)N—C₁-C₃-alkyl, phenyl-Z and heterocyclyl-Z, wherein heterocyclyl is a 5- or 6-membered monocyclic or 8-, 9- or 10-membered bicyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, wherein phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups R′, which are identical or different; R⁷ is selected from the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-haloalkoxy-C₁-C₄-alkyl; n is 0, 1 or 2; k is 0, 1 or 2; R′, R¹¹, R²¹ independently of each other are selected from the group consisting of halogen, NO₂, CN, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-halocycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₆-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylthio-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy, C₃-C₇-cycloalkoxy and C₁-C₆-haloalkyloxy, or two vicinal radicals R′, R¹ or R²¹ together may form a group ═O; Z, Z¹, Z² independently of each other are selected from the group consisting of a covalent bond and C₁-C₄-alkanediyl; Z^(2a) is selected from the group consisting of a covalent bond, C₁-C₄-alkanediyl, O—C₁-C₄-alkanediyl, C₁-C₄-alkanediyl-O and C₁-C₄-alkanediyl-O—C₁-C₄-alkanediyl; R^(b), R^(1b), R^(2b) independently of each other are selected from the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, phenyl and heterocyclyl, wherein heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, wherein phenyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(c), R^(2c) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl, benzyl and heterocyclyl, wherein heterocyclyl is a 5- or 6-membered monocyclic saturated, partially unsaturated or aromatic heterocycle, which contains 1, 2, 3 or 4 heteroatoms as ring members, which are selected from the group consisting of O, N and S, wherein phenyl, benzyl and heterocyclyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(d), R^(2d) independently of each other are selected from the group consisting of C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(e), R^(f) independently of each other are selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or R^(e), R^(f) together with the nitrogen atom to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(2e), R^(2f) independently of each other have the meanings given for R^(e), R^(f); R^(g) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(h) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₇-cycloalkyl, C₃-C₇-cycloalkyl-C₁-C₄-alkyl, wherein the C₃-C₇-cycloalkyl groups in the two aforementioned radicals are unsubstituted or partially or completely halogenated, C₁-C₆-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-haloalkenyl, C₂-C₆-alkynyl, C₂-C₆-haloalkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylcarbonyl, a radical C(═O)—R^(k), phenyl and benzyl, wherein phenyl and benzyl are unsubstituted or substituted by 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy, or R^(g), R^(h) together with the nitrogen atom to which they are bound may form a 5-, 6 or 7-membered, saturated or unsaturated N-bound heterocyclic radical, which may carry as a ring member a further heteroatom selected from the group consisting of O, S and N and which is unsubstituted or may carry 1, 2, 3 or 4 groups, which are identical or different and selected from the group consisting of ═O, halogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy and C₁-C₄-haloalkoxy; R^(2g), R^(2h) independently of each other have the meanings given for R^(g), R^(h); R^(k) has the meanings given for R^(c); an N-oxide or an agriculturally suitable salt thereof.
 21. The compound of claim 20, wherein R¹ is selected from the group consisting of halogen, nitro, C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio and C₁-C₄-alkylsulfonyl.
 22. The compound of claim 20, wherein X is N.
 23. The compound of claim 20, wherein X is CR² and R² is different from hydrogen.
 24. The compound of claim 20, wherein X is CR² and R² is hydrogen.
 25. The compound of claim 23, wherein R² is selected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₃-alkoxy-C₁-C₃-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), wherein k is 0, 1 or 2, isoxazolyl and isoxazolinyl, wherein the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from the group consisting of halogen and C₁-C₄-alkyl.
 26. The compound of claim 20, wherein R³ is selected from the group consisting of hydrogen, halogen, CN, NO₂, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, C₁-C₄-alkylS(O)₂ and C₁-C₄-haloalkyl-S(O)₂.
 27. The compound of claim 20, wherein R⁴ is selected from the group consisting of hydrogen, CHF₂, CF₃, CN, NO₂, CH₃ and halogen.
 28. The compound of claim 20, wherein R⁵ is selected from the group consisting of CHF₂, CF₃ and halogen.
 29. The compound of claim 20, wherein R⁵ is selected from the group consisting of chlorine and fluorine.
 30. The compound of claim 20, wherein R⁶ is hydrogen.
 31. The compound of claim 20, wherein R⁶ is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, R^(d)O—C(═O)—C₁-C₃-alkyl, and phenyl-Z and wherein phenyl is unsubstituted or substituted by 1, 2, 3 or 4 groups R′, which are identical or different.
 32. The compound of claim 20, wherein R⁷ is selected from the group consisting of C₁-C₄-alkyl, C₃-C₇-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy and C₁-C₄-alkoxy-C₁-C₄-alkyl.
 33. The compound of claim 20, wherein X is CR² and the variables R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings: R¹ is selected from the group consisting of halogen, nitro, cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkyl-S(O)₂; R² is selected from the group consisting of hydrogen, halogen, C₁-C₆-alkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₁-C₄-haloalkoxy-C₁-C₄-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₁-C₄-alkoxy, C₁-C₃-alkoxy-C₁-C₃-alkoxy, C₁-C₄-haloalkoxy, C₃-C₆-alkenyloxy, C₃-C₆-alkynyloxy, C₃-C₆-haloalkenyloxy, C₃-C₆-haloalkynyloxy, C₁-C₄-alkoxycarbonyl, C₁-C₄-alkyl-S(O)_(k) and C₁-C₄-haloalkyl-S(O)_(k), wherein k is 0, 1 or 2, isoxazolyl and isoxazolinyl, wherein the last two mentioned radicals may be unsubstituted or carry 1 or 2 radicals selected from the group consisting of halogen and C₁-C₄-alkyl; R³ is selected from the group consisting of hydrogen, halogen, CN, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂; R⁴ is selected from the group consisting of hydrogen and halogen; R⁵ is selected from the group consisting of halogen, CHF₂ and CF₃; R⁶ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and phenyl-C₁-C₂-alkyl; R⁷ is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₂-alkoxy-C₁-C₂-alkyl.
 34. The compound of claim 20, wherein X is CR² and the variables R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings: R¹ is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl; R² is selected from the group consisting of hydrogen, chlorine, fluorine, methyl, methylsulfonyl, methylsulfinyl, methylsulfanyl, 3-isoxazolinyl, 5-methyl-3-isoxazolinyl, 5-isoxazolinyl, 3-methyl-5-isoxazolinyl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 5-isoxazolyl and 3-methyl-5-isoxazolyl; R³ is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl; R⁴ is selected from the group consisting of hydrogen, chlorine and fluorine; R⁵ is selected from the group consisting of chlorine and fluorine; R⁶ is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl; R⁷ is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxymethyl, methoxyethyl and ethoxymethyl;
 35. The compound of claim 20, wherein X is N and the variables R¹, R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings: R¹ is selected from the group consisting of halogen, nitro, cyclopropyl, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy-C₁-C₄-alkyl, C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkoxy-C₁-C₄-alkyl and C₁-C₄-alkyl-S(O)₂; R³ is selected from the group consisting of hydrogen, halogen, CN, C₁-C₄-haloalkyl and C₁-C₄-alkyl-S(O)₂; R⁴ is selected from the group consisting of hydrogen and halogen; R⁵ is selected from the group consisting of halogen, CHF₂ and CF₃; R⁶ is selected from the group consisting of hydrogen, C₁-C₄-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₁-C₄-alkoxycarbonyl-C₁-C₄-alkyl and phenyl-C₁-C₂-alkyl; R⁷ is selected from the group consisting of C₁-C₄-alkyl, C₁-C₄-alkoxy and C₁-C₂-alkoxy-C₁-C₂-alkyl.
 36. The compound of claim 20, wherein X is N and the variables R¹, R³, R⁴, R⁵, R⁶ and R⁷ have the following meanings: R¹ is selected from the group consisting of chlorine, nitro, methyl, trifluoromethyl and methylsulfonyl; R³ is selected from the group consisting of hydrogen, fluorine, chlorine, CN, trifluoromethyl, and methylsulfonyl; R⁴ is selected from the group consisting of hydrogen, chlorine and fluorine; R⁵ is selected from the group consisting of chlorine and fluorine; R⁶ is selected from the group consisting of hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, prop-2-enyl, prop-2-ynyl, methoxycarbonylmethyl and benzyl; R⁷ is selected from the group consisting of methyl, ethyl, methoxy, ethoxy, methoxymethyl, methoxyethyl and ethoxymethyl;
 37. A composition comprising at least one compound of claim 20 and at least one auxiliary, which is customary for formulating crop protection compounds.
 38. A method for controlling unwanted vegetation, comprising allowing a herbicidally effective amount of at least one compound of claim 20 to act on plants, their seed and/or their habitat.
 39. A method for controlling unwanted vegetation, comprising allowing a herbicidally effective amount of the composition of claim 37 to act on plants, their seed and/or their habitat. 